Anhydro Sugars Research Articles

Methylation-GC-MS/FID-Based Glycosidic Linkage Analysis of Unfractionated Polysaccharides in Red Seaweeds.

Glycosidic linkage analysis was conducted on the unfractionated polysaccharides in alcohol-insoluble residues (AIRs) prepared from six red seaweeds (Gracilariopsis sp., Prionitis sp., Mastocarpus papillatus, Callophyllis sp., Mazzaella splendens, and Palmaria palmata) using GC-MS/FID analysis of partially methylated alditol acetates (PMAAs). The cell walls of P. palmata primarily contained mixed-linkage xylans and small amounts of sulfated galactans and cellulose. In contrast, the unfractionated polysaccharides of the other five species were rich in galactans displaying diverse 3,6-anhydro-galactose and galactose linkages with varied sulfation patterns. Different levels of cellulose were also observed. This glycosidic linkage method offers advantages for cellulose analysis over traditional monosaccharide analysis that is known for underrepresenting glucose in crystalline cellulose. Relative linkage compositions calculated from GC-MS and GC-FID measurements showed that anhydro sugar linkages generated more responses in the latter detection method. This improved linkage workflow presents a useful tool for studying polysaccharide structural variations across red seaweed species. Furthermore, for the first time, relative linkage compositions from GC-MS and GC-FID measurements, along with normalized FID and total ion current (TIC) chromatograms without peak assignments, were analyzed using principal component analysis (PCA) as a proof-of-concept demonstration of the technique's potential to differentiate various red seaweed species.

Influence of alkali and alkali earth metals on pyrolysis of tobacco waste

The effect of alkali and alkali earth metals on pyrolysis behavior of tobacco was revealed in this paper. Four alkali and alkali earth metal ions (Na+, K+, Ca2+, and Mg2+) were used to impregnate acid-washed tobacco. The addition of alkali and alkali earth metal ions in acid-washed tobacco increases the relative content of ketones, acids, nitrogen containing compounds, and esters, while inhibit the formation of anhydro sugars and aldehydes. The generation of solid residues is enhanced by the presence of alkali and alkali earth metal ions and the increase of K+ concentration. The addition of 0.5 mmol K+/g can increase the yield of solid residues from 13.7 wt% to 20.2 wt%. The increase of K+ concentration promotes the conversion of anhydro sugars to ketones. The effect of hot water-wash, acid-wash, and acid-infuse, which can control the concentration of alkali and alkali earth metal ions in the tobacco, on the product distribution of tobacco pyrolysis were also discussed. Acid-wash method and hot water-wash method promote the production of carbohydrate derivatives and inhibit the generation of nitrogen-containing products. After nitric acid-wash and hot water-wash pretreatment, the relative content of nitrogen-containing products decreased from 52.1% to 6.2% and 4.3%, respectively. Compared with inorganic acid-wash pretreatment method, organic acid-wash pretreatment method has weaker inhibition on nitrogen-containing products. Organic acid-wash pretreatment method promoted the formation of aromatics and aldehydes. Prewash methods facilitate the thermal decomposition of tobacco. The results from this study suggests that feedstock pretreatment could be used as a strategy of controlling aroma compounds formation from tobacco.

A fast, single column high-performance anion exchange chromatography with pulsed amperometric detection method for the determination of saccharides in atmospheric aerosol samples.

Saccharides, especially anhydro sugars present in atmospheric aerosols, can be used as tracers to track sources of atmospheric aerosols. High-performance anion-exchange chromatography with pulsed amperometric detection is a commonly used technique for determining these saccharides, but the reported methods suffer from three drawbacks. First, to achieve separation of the complete set of atmospheric saccharides, run times are very long, typically longer than 60 minutes. Second, some methods require two columns to achieve the desired separation. Finally, in an era when electrolytic eluent preparation allows for excellent precision and accuracy, these methods require manually prepared eluents, which can lead to separation inconsistency for closely eluting analytes. These drawbacks make existing methods difficult to automate. To address this issue, we developed a fast method that uses only a single column for separation and electrolytically generated eluent that resolves 12 key atmospheric aerosol saccharides in 20 minutes. The resolved saccharides include anhydro sugars (levoglucosan, galactosan, and mannosan), sugar alcohols (erythritol, xylitol, and mannitol), and mono-/disaccharides (arabinose, galactose, glucose, mannose, fructose, and sucrose). To our knowledge, this report is the first instance of achieving such a significant reduction in run time with good resolution for this set of saccharides.

Co-pyrolysis of cellulose and urea blend: Nitrogen conversion and effects of parameters on nitrogenous compounds distributions in bio-oil

This paper aimed at investigating the co-pyrolysis behavior of cellulose and urea in a fixed bed reactor under N2 atmosphere. The effects of the proportions of urea in blend and pyrolysis temperatures on the char and the components of bio-oil were investigated. When the proportion of urea was 20 %, the peak area of anhydro sugars was 28.66 % higher than that when the proportion of urea was 0%. Furans and carbonyls were the key intermediates for the formation of nitrogenous heterocyclic compounds (NHCs) from cellulose. The NHCs in the obtained bio-oil mainly are pyrroles, pyrimidines, pyridines, imidazoles and pyrazines. Higher temperature (600℃) was unfavorable for improving the selectivity of NHCs. Co-pyrolysis of cellulose and urea can introduce abundant nitrogen and nitrogenous functional groups into char. In addition, residuals obtained at different residence times have also been characterized by element analysis and FTIR. The results showed that both the amount and the kind of functional groups in the residuals were reduced with the residence time increasing. High value NHCs and nitrogen-rich char were generated by co-pyrolysis of cellulose and urea. Finally, the possible reactions for the generation of NHCs in the bio-oil were given.

Effects of KCl and CaCl2 on the evolution of anhydro sugars in reaction intermediates during cellulose fast pyrolysis

Reaction intermediates mainly consisting of anhydro sugars are the crucial transitional stage connecting the cellulose feedstock and the three phases of products during pyrolysis. For the first time, the effects of KCl and CaCl2 on the evolution of anhydro sugars in reaction intermediates were examined by using levoglucosan pyranose (LGA_Pyran), maltosan and cyclodextrin as model compounds. These compounds were subjected to fast pyrolysis on a Py-GC/MS, where dry samples were heated at a heating rate of 10 °C/s to 500 °C with a holding time of 20 s at 500 °C. The results indicated that KCl had a stronger inhibitory effect than CaCl2 on LGA_Pyran formation during cellulose fast pyrolysis. However, during the pyrolysis of the oligosaccharides, the catalytic effects of KCl were weakened by the low degree of polymerization and the lack of reducing ends, while the catalytic effects of CaCl2 were enhanced by a better distribution. This led to the reverse order of their effects on LGA_Pyran formation. Furthermore, much higher char yields from oligosaccharides under catalysis of CaCl2 than under the catalysis of KCl indicate the prominent influence of CaCl2 on the secondary reactions of reaction intermediates leading to secondary char.

Heat Treatment Effect on Lignin and Carbohydrates in Corsican Pine Earlywood and Latewood Studied by PY–GC–MS Technique

Lignin-derived degradation products from non-treated (NT) and heat-treated (T) Corsican pine (Pinus nigra subsp. laricio) obtained by pyrolysis–gas chromatography–mass spectrometry (Py–GC–MS) were investigated, whereby the earlywood (EW) and latewood (LW) parts of the annual ring were considered separately. The data evaluation was done by principal component analysis (PCA) and the Kruskal–Wallis test. There are no differences in the pyrolysis products composition between EW and LW, but NT and T samples were discernible by PCA applied to Py–GC–MS data. Less phenols with longer chains (4-vinylguaiacol, and trans-isoeugenol) than those with shorter chains (guaiacol, 4-methylguaiacol) and an increase of anhydrosugar (AHS) were found among the pyrolysis products after heat treatment. These signs for autocondensation and side chain cleavages in the lignin during heat treatment were more evident in the EW than in the LW and for the crystallization of cellulose. A slight decrease of the carbohydrate/lignin ratio (C/L) after heat treatment indicates a greater degradation of carbohydrates compared to lignin. The relation of pyrolysis products of lignin and mechanical properties of wood was evaluated by regression analysis. An inverse correlation between short-chain phenols and MOE and a direct correlation between long-chain phenols and compression strength was found in case of NT wood, while a weak positive correlation could be observed between short-chain phenols and the density in T wood.

Molecular composition of organic aerosol over an agricultural site in North China Plain: Contribution of biogenic sources to PM2.5

Sugars and biogenic secondary organic aerosols (BSOAs) are substantial components of particulate organic matter, which affects regional and global air quality and climate. Fine particulate matter (PM2.5) samples were collected from 20 June to 30 July 2015 on a diurnal/nocturnal cycle in Yucheng, China in the North China Plain. The PM2.5 samples were analyzed for sugars and SOA tracers derived from biogenic volatile organic compounds (BVOCs) and other compounds, such as water soluble ions, element carbon (EC), organic carbon (OC) and water soluble organic carbon (WSOC). The quantified organic components accounted for 4.7% and 0.4% of the OC and PM2.5, respectively. SOA tracer concentrations were weakly higher during the day (101.6 ± 61.7 ng m−3) than at night (90.2 ± 41.5 ng m−3)(t = 0.610, P > 0.05), whereas sugar showed higher concentrations at night (227.0 ± 196.9 ng m−3) than during the day (177.9 ± 145.4 ng m−3)(t = −1.329, P > 0.05). Anhydro sugar (mannosan, galactosan, and levoglucosan) were the main components of the measured sugars and accounted for 58.5% and 75.6% of the daytime and nighttime measurements. The levoglucosan/mannosan ratios were 20.2 ± 12.9 and 17.6 ± 9.1 for the daytime and nighttime samples, respectively, indicating that crop residues, herbaceous plants and hardwood were the dominant types of biomass burned in the Yucheng region. Isoprene SOA tracers exhibited the highest levels among the measured SOA tracers, followed by α-pinene SOA tracers. The concentration of BSOC estimated using the tracer method was 3.9–1817.5 ng C m−3 and accounted for 0.1–26.0% of the OC. A clear negative correlation (r = 0.53) between isoprene-derived SOA and in-situ pH demonstrated that acid-catalyzed heterogeneous reactions can significantly enhance SOA mass. In addition, isoprene-derived SOA increased with the relative humidity (RH) when the RH was lower than 50%, whereas it decreased when the RH was higher than 50%.

Biomass catalytic fast pyrolysis over hierarchical ZSM-5 and Beta zeolites modified with Mg and Zn oxides

Hierarchical ZSM-5 and Beta zeolites, loaded with MgO and ZnO, have been explored for the catalytic fast-pyrolysis of eucalyptus woodchips. These materials exhibit a high dispersion of the MgO or ZnO phases, which is probably due to the presence of a hierarchical porosity with both micro- and mesopores in the zeolitic supports. The incorporation of these metal oxides led to a significant reduction in the textural properties and to changes in the acidic properties of the parent zeolites. Thus, a decrease in the concentration of Bronsted acid sites was observed, which was accompanied by the generation of additional Lewis acid sites with medium strength. In addition, the incorporation of metal oxide promotes the formation of significant amount of basic sites, especially for the samples loaded with MgO. Catalytic fast pyrolysis experiments of eucalyptus woodchips were performed in a fixed bed reactor at 500 °C and atmospheric pressure under a nitrogen flow. In comparison with non-catalytic fast pyrolysis, the use of zeolitic catalysts caused a decrease in the bio-oil* (water free basis bio-oil) production due to enhanced formation of gases, as well as coke deposition on the catalyst. However, the quality of the bio-oil* was enhanced since the catalysts were able to decrease its oxygen content. In this way, h-ZSM-5-based catalysts showed a clearly deeper deoxygenation degree compared to those having h-Beta as support, with very low content of anhydro sugars and the formation of a significant amount of aromatics. Regarding the effect of the metal oxide phase, MgO-loaded samples provided bio-oil* with enhanced energy yields and lower oxygen content, probably due to the adequate balance of Lewis acid and basic sites. Likewise, significant differences were observed among the catalysts regarding the deoxygenation pathways and the compounds families present in the bio-oil*.

Thermochemical valorization of camelina straw waste via fast pyrolysis

The present work investigates the thermochemical valorization of camelina straw, which is a waste generated during the harvesting of Camelina sativa, an oilseed crop for the production of biodiesel or hydrotreated vegetable oil (HVO). In particular, it is focused on obtaining bio-oil via thermal or catalytic fast pyrolysis, which would be the first stage on a sequence of chemical processes for biofuel production. The catalytic interference of the inorganic matter present in the biomass was studied by preparing a batch of de-ashed camelina straw by washing with diluted nitric acid. Chemical analysis revealed this treatment effectively removed alkaline (K and Na) and alkaline earth (Ca and Mg) metals. Pyrolysis of de-ashed camelina straw led to higher mass and energy yields of bio-oil in water-free basis (bio-oil*), but with higher oxygen concentration. Catalytic pyrolysis over HZSM-5 was also studied in both raw and de-ashed feedstocks. This catalyst promoted mainly decarbonylation and decarboxylation reactions of the pyrolysis vapors, leading to much higher gas yields and lower of bio-oil*, but with better quality. Catalytic pyrolysis of untreated camelina straw exhibited a synergetic effect between both the inorganic matter and the external HZSM-5 catalyst, so that bio-oil* yield was the lowest (20 wt%) due to an extensive deoxygenation (18 wt% oxygen content), which resulted in the highest HHV obtained (37.3 MJ/kgdb). Significant differences were also found on the molecular composition of the bio-oils* with larger proportion of anhydro sugars when the biomass was de-ashed, while HZSM-5 strongly promoted the formation of oxygenated aromatics and aromatic hydrocarbons.

Isosorbide and dimethyl carbonate: a green match.

In this review the reactivity of the bio-based platform compounds D-sorbitol and isosorbide with green reagents and solvent dimethyl carbonate (DMC) is reported. Dehydration of D-sorbitol via DMC in the presence of catalytic amounts of base is an efficient and viable process for the preparation of the industrially relevant anhydro sugar isosorbide. This procedure is “chlorine-free”, one-pot, environmental friendly and high yielding. The reactivity of isosorbide with DMC is equally interesting as it can lead to the formation of dicarboxymethyl isosorbide, a potential monomer for isosorbide-based polycarbonate, and dimethyl isosorbide, a high boiling green solvent. The peculiar reactivity of isosorbide and the non-toxic properties of DMC represent indeed a green match leading to several industrial appealing potential applications.

The Construction of Anhydro Monosaccharides

AbstractAnhydro monosaccharide is a specific and distinctive category of carbohydrates, which is found in many naturally derived and artificial bioactive substrates. In the field of organic chemistry, some anhydro sugars can be used as common synthons to construct different carbohydrate structures. The development of efficient methodologies for the construction of various anhydro sugar fragments is very important in carbohydrate chemistry, which has attracted considerable attention in the past few years. This review mainly covers the development of new synthetic methods since 2000 and gives an overview of the development in the formation of anhydro monosaccharide structures. It systematically summarizes all methods to establish an intramolecular ether bridge in furanose and pyranose structures, which are the most commonly used monosaccharide fragments in carbohydrate chemistry.

Pyrolysis behaviors of four O-acetyl-preserved hemicelluloses isolated from hardwoods and softwoods

The pyrolysis mechanisms of O-acetyl-preserved hemicelluloses isolated from both hardwoods and softwoods have been investigated. Their chemical structures, pyrolysis kinetics, pyrolytic product distributions, and pyrolytic gaseous evolutions have been systematically studied. Hardwood hemicellulose was mainly composed of 4-O-methyl-d-glucurono-d-xylan and had high contents of O-acetyl and uronic acid units, whereas softwood hemicelluloses were composed of d-galacto-d-gluco-d-mannan and l-arabino-4-O-methyl-d-glucurono-d-xylan. A double-Gaussian distributed activation energy model has been introduced to simulate the pyrolysis kinetics. Hardwood hemicellulose pyrolysis showed lower activation energies than softwood hemicellulose pyrolysis. Hardwood hemicellulose pyrolysis mainly yielded furfural and acids, whereas for softwood hemicellulose pyrolysis, 5-hydroxymethylfurfural and anhydro sugars were typical products. The evolution behaviors of H2O, CO2, CO, and acids from the pyrolyzes of the four hemicelluloses are discussed.

The neighbouring effect of isosorbide and its epimers in their reactions with dimethyl carbonate

– The reactions of isosorbide and its epimers, isomannide and isoidide, with dimethyl carbonate have been herein investigated as easy access to bio-based products by a free-halogen chemistry approach. Isosorbide and its epimers show a different reactivity in bimolecular nucleophilic substitution with DMC. Carboxymethylation reaction was carried out in the presence of DMC and a weak base resulting in the high-yielding synthesis of dicarboxymethyl derivatives. Isomannide was the most reactive anydro sugars due to the less sterically hindered exo position of the OH groups. On the other hand, methylation of isosorbide and its epimers, conducted in the presence of a strong base and DMC, showed the higher reactivity of the endo hydroxyl group, isoidide being the most reactive epimer. This result has been ascribed to the neighbouring effect due to the combination of the oxygen in β-position and the intramolecular hydrogen bond within the anhydro sugar structure. Methylation reactions were also conducted in autoclave at high temperature with the amphoteric catalyst hydrotalcite using DMC as reagent and solvent. In this case, the reactivity of the epimers resulted quite different with isosorbide being the most reactive reagent possibly as a result of the structure of hydrotalcite comprising of both acidic and basic sites. The neighbouring effect was observed with good evidence in these methylation reactions.

The neighbouring effect of isosorbide and its epimers in their reactions with dimethyl carbonate

– The reactions of isosorbide and its epimers, isomannide and isoidide, with dimethyl carbonate have been herein investigated as easy access to bio-based products by a free-halogen chemistry approach. Isosorbide and its epimers show a different reactivity in bimolecular nucleophilic substitution with DMC. Carboxymethylation reaction was carried out in the presence of DMC and a weak base resulting in the high-yielding synthesis of dicarboxymethyl derivatives. Isomannide was the most reactive anydro sugars due to the less sterically hindered exo position of the OH groups. On the other hand, methylation of isosorbide and its epimers, conducted in the presence of a strong base and DMC, showed the higher reactivity of the endo hydroxyl group, isoidide being the most reactive epimer. This result has been ascribed to the neighbouring effect due to the combination of the oxygen in β-position and the intramolecular hydrogen bond within the anhydro sugar structure. Methylation reactions were also conducted in autoclave at high temperature with the amphoteric catalyst hydrotalcite using DMC as reagent and solvent. In this case, the reactivity of the epimers resulted quite different with isosorbide being the most reactive reagent possibly as a result of the structure of hydrotalcite comprising of both acidic and basic sites. The neighbouring effect was observed with good evidence in these methylation reactions.

The neighbouring effect of isosorbide and its epimers in their reactions with dimethyl carbonate

Abstract The reactions of isosorbide and its epimers, isomannide and isoidide, with dimethyl carbonate have been herein investigated as easy access to bio-based products by a free-halogen chemistry approach. Isosorbide and its epimers show a different reactivity in bimolecular nucleophilic substitution with dimethyl carbonate (DMC). Carboxymethylation reaction was carried out in the presence of DMC and a weak base resulting in the high-yielding synthesis of dicarboxymethyl derivatives. Isomannide was the most reactive anhydro sugar due to the less sterically hindered exo position of the OH groups. On the other hand, methylation of isosorbide and its epimers, conducted in the presence of a strong base and DMC, showed the higher reactivity of the endo hydroxyl group, isoidide being the most reactive epimer. This result has been ascribed to the neighboring effect due to the combination of the oxygen in β-position and the intramolecular hydrogen bond within the anhydro sugar structure. Methylation reactions were also conducted in autoclave at high temperature with the amphoteric catalyst hydrotalcite using DMC as reagent and solvent. In this case, the reactivity of the epimers resulted quite differently with isosorbide being the most reactive reagent possibly as a result of the structure of hydrotalcite comprising of both acidic and basic sites. The neighboring effect was observed with good evidence in these methylation reactions.

The neighbouring effect of isosorbide and its epimers in their reactions with dimethyl carbonate

ABSTRACT – The reactions of isosorbide and its epimers, isomannide and isoidide, with dimethyl carbonate have been herein investigated as easy access to bio-based products by a free-halogen chemistry approach. Isosorbide and its epimers show a different reactivity in bimolecular nucleophilic substitution with DMC. Carboxymethylation reaction was carried out in the presence of DMC and a weak base resulting in the high-yielding synthesis of dicarboxymethyl derivatives. Isomannide was the most reactive anydro sugars due to the less sterically hindered exo position of the OH groups. On the other hand, methylation of isosorbide and its epimers, conducted in the presence of a strong base and DMC, showed the higher reactivity of the endo hydroxyl group, isoidide being the most reactive epimer. This result has been ascribed to the neighbouring effect due to the combination of the oxygen in β-position and the intramolecular hydrogen bond within the anhydro sugar structure. Methylation reactions were also conducted in autoclave at high temperature with the amphoteric catalyst hydrotalcite using DMC as reagent and solvent. In this case, the reactivity of the epimers resulted quite different with isosorbide being the most reactive reagent possibly as a result of the structure of hydrotalcite comprising of both acidic and basic sites. The neighbouring effect was observed with good evidence in these methylation reactions.

An improved synthesis of 3,6-anhydro-d-glucal and a study of its unusual chemical reactivity

6-O-Tosyl-d-glucal 1 upon treatment with excess LiAlH4 unexpectedly gave 3,6-anhydro-d-glucal 2 as a major product in good yield. A crystal structure was obtained. Reaction of the anhydride 2 with N-iodosuccinimide (NIS) in excess methanol resulted in the formation of diastereomeric 2-deoxy-2-iodoglycosides. Addition of ceric (IV) ammonium nitrate and thiophenol to a solution of 2 in acetonitrile gave a mixture of 2-deoxy and 2,3-unsaturated thioglycosides. Reaction of 1,2:3,4-di-O-isopropylidine-α-d-galactopyranose with the anhydro sugar 2 in the presence of N-iodosuccinimide did not give the expected iodoglycoside mixture, but instead gave an unusual 1,4:3,6-dianhydride 7 as the major product.

Catalytic Pyrolysis of Raw and Thermally Treated Cellulose Using Different Acidic Zeolites

Fast pyrolysis of biomass using zeolite catalyst has shown to be effective in improving aromatic production. This study focuses on aromatic production through catalytic pyrolysis of major biomass constituent i.e., cellulose. Furthermore, cellulose was torrefied to understand torrefaction’s effect on pyrolysis products. The influence of SiO2/Al2O3 ratios of zeolite (ZSM-5) catalyst on aromatic production during pyrolysis of raw and torrefied cellulose was investigated. Results showed that the catalyst acidity played a pivotal role in eliminating anhydro sugars and other oxygenated compounds while producing more aromatics. The maximum aromatic yield (~25 wt%) was obtained when ZSM-5 with the highest acidity (SiO2/Al2O3 = 30) was used, while the lowest yield (7.99 wt%) was obtained when the least acidic catalyst was used (SiO2/Al2O3 = 280) for raw cellulose pyrolysis. Torrefaction process showed to have positive effect on the aromatic production from pyrolysis. There were no aromatics produced from pyrolysis of raw cellulose in the absence of catalyst, whereas significant amount of aromatic compounds were produced from both catalytic and noncatalytic pyrolyses of torrefied cellulose. The aromatic hydrocarbons produced from catalytic pyrolysis of torrefied cellulose were 5 % more than those produced from raw cellulose at the highest temperature and catalyst acidity (SiO2/Al2O3 = 30).

Synthesis of a new 2‐amino‐glycan, poly‐(1→6)‐α‐D‐mannosamine, by ring‐opening polymerization of 1,6‐anhydro‐mannosamine derivatives

AbstractA stereoregular 2‐amino‐glycan composed of a mannosamine residue was prepared by ring‐opening polymerization of anhydro sugars. Two different monomers, 1,6‐anhydro‐2‐azido‐mannose derivative (3) and 1,6‐anhydro‐2‐(N, N‐dibenzylamino)‐mannose derivative (6), were synthesized and polymerized. Although 3 gave merely oligomers, 6 was promptly polymerized into high polymers of the number‐average molecular weight (Mn) of 2.3 × 104 to 2.9 × 104 with 1,6‐α stereoregularity. The differences of polymerizability of 3 and 6 from those of the corresponding glucose homologs were discussed. It was found that an N‐benzyl group is exceedingly suitable for protecting an amino group in the polymerization of anhydro sugars of a mannosamine type. The simultaneous removal of O‐ and N‐benzyl groups of the resulting polymers was achieved by using sodium in liquid ammonia to produce the first 2‐amino‐glycan, poly‐(1→6)‐α‐D‐mannosamine, having high molecular weight through ring‐opening polymerization of anhydro sugars.© 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

ChemInform Abstract: Syntheses with Anhydro Sugars. Part 39. The Synthesis of 4-O- Oligoethylene Glycol Derivatives of 1,6-Anhydro-β-D-glucopyranose and Crown-Ethers Formed by Their Intramolecular Cyclization.

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