Deoxy Glycosides Research Articles

Catalytic ceric ammonium nitrate mediated synthesis of 2-deoxy-1-thioglycosides

Synthesis of 2-deoxy-1-thioglycosides from glycals, mediated by catalytic amounts of ceric ammonium nitrate is reported. Apart from the 2-deoxy-1-thioglycosides, formation of the 2,3-unsaturated enose, corresponding to the Ferrier product, is also observed, especially for the glucal substrates. A radical oxocarbenium ion and a thiolate intermediates are most likely to mediate the reaction. Upon synthesis of 2-deoxy-1-thioglycosides, few representative glycosylation reactions with both aglycosyl and glycosyl acceptors were performed and α-anomeric 2-deoxy glycosides were obtained exclusively.

Total synthesis of everninomicin 13,384-1--Part 4: explorations of methodology; stereocontrolled synthesis of 1,1'-disaccharides, 1,2-seleno migrations in carbohydrates, and solution- and solid-phase synthesis of 2-deoxy glycosides and orthoesters.

Methods for the stereocontrolled construction of 1,1'-disaccharides, 2-deoxy glycosides, and orthoesters are reported. Specifically, a tin-acetal moiety was utilized to fix the anomeric stereochemistry of a carbohydrate acceptor leading to an efficient and stereoselective synthesis of 1,1'-disaccharides, while a newly discovered 1,2-phenylseleno migration reaction in carbohydrates opened entries to 2-deoxy glycosides and orthoesters. Thus, reaction of 2-hydroxy phenylselenoglycosides with DAST led to 2-phenylselenoglycosyl fluorides which reacted with carbohydrate acceptors to afford, stereoselectively, 2-phenylselenoglycosides. The latter compounds could be reductively deselenated to 2-deoxy glycosides or oxidatively converted to orthoesters via the corresponding ketene acetals.

Synthesis of Deoxy Glycosides Under Neutral Conditions in LiClO4/Solvent Mixtures

Synthesis of Deoxy Glycosides Under Neutral Conditions in LiClO4/Solvent Mixtures

Artificial deoxy glycosides of anthracyclines

AbstractIn Lewis acid mediated allylic rearrangement reactions of L‐rhamnal (1) and L‐fucal (2) with daunomycinon (6) 2′‐deoxyhex‐2′‐enopyranosides have been obtained exclusively. Furthermore, glycals 1 and 4 have been treated with the glycosyl acceptors 6, 7, and 9 and N‐iodosuccinimide (NIS) to produce the corresponding α‐configurated 2′‐deoxy‐2′‐iodo glycosides. Among these, 16 represents a bis (glycoside) with both benzylic aglycon positions substituted. In none of the above cases has a substantial amount of β‐glycoside been detected. Attempts to convert ε‐isorhodomycinon (8) into a glycoside on a preparative scale, under Lewis acid conditions have been unsuccessful. However, the α‐glycoside 13 has been obtained by the Helferich method.

ChemInform Abstract: Syntheses of Deoxy Oligosaccharides

This paper focusses on stereoselective syntheses of deoxy oligosaccharides which are an integral part of a number of antibiotics and cytostatics. Following a short review on the biosynthesis of these sugars, the general techniques including classical methods as well as recent stereospecific procedures for the preparation of deoxy glycosides are outlined.

ChemInform Abstract: A NOVEL STEREOSELECTIVE ROUTE TO ALKYL 2‐DEOXY‐β‐D‐GLUCOSIDES VIA S‐(2‐DEOXY‐α‐GLUCOSYL) PHOSPHORODITHIOATES

AbstractDas Glucal (I) wird mit (II) zum α‐Dialkyldithiophosphoryl‐glucosid (III) umgesetzt, aus dem durch Alkoholyse in Gegenwart von Basen die 2‐Desoxy‐β‐glycoside (IVa) mit freier OH‐Gruppe erhalten werden.

A Novel Stereoselective Route to Alkyl 2-Deoxy-β-D-glucosides via S-(2-Deoxy-α-glucosyl) Phosphorodithioates

Abstract Intense interest in sugar components of anthracycline antibiotics and antitumor drugs generated a need for stereoselective methods of synthesis of 2-deoxy sugar glycosides. Although several efficient procedures leading to 2-deoxy-α-glycosides were elaborated, there is no satisfactory general procedure leading to the β-anomers. The methods described are not stereoselective and involve separation of anomeric intermediates of glycosides.