O-benzyl Ethers Research Articles

The preparation and phosphorylation of 2,5- and 1 d-2,6-di- O-benzyl- myo-inositol

1,3,4,6-Tera- O-allyl- myo-inositol was converted into the 2,5-di- O-benzyl- and 2,5-di- O-p-methoxybenzyl ethers, and the products were deallylated to give the 2,5-di- O-benzyl (and p-methoxybenzyl) ethers of myo-inositol, which were converted into the mono- O-isopropylidene derivatives. Both the 2,5-di- O-benzyl ether and its mono- O-isopropylidene derivative were converted into the crystalline octa(2-cyanoethyl) ester of 2,5-di- O-benzyl- myo-inositol 1,3,4,6-tetrakisphosphate. (±)-1,3,4,5-Tetra- O-allyl- myo-inositol was converted into (±)-2,4-di- O-benzyl- myo-inositol which gave a separable mixture of the 1,6- and 5,6- O-isopropylidene derivatives. The 1,6- O-isopropylidene derivative was resolved via (−)- and (+)-ω-camphanates and was also converted into (±)-2,6-di- O-benzyl-1,5-di- O-p-methoxybenzyl- myo-inositol, which was resolved via the (−)-ω-camphanates. The 5,6- O-isopropylidene derivative and 1,3-di- O-allyl- myo-inositol were converted into (±)-1,3-di- O-allyl-2,6-di- O-benzyl- myo-inositol, which was resolved as the (−)-ω-camphanates. 1 d-1,3,4,5-Tetra- O-allyl- myo-inositol and the above described, relevant diaste reoisomers were converted into 1 d-2,6-di- O-benzyl- myo-inositol which gave the syrupy octabenzyl ester of 1 d-2,6-di- O-benzyl- myo-inositol 1,3,4,5-tetrakisphosphate.

Gas chromatography—mass spectrometry of d1-, keto- and hydroxycarboxylic acid benzyl esters

The benzyl esters of di-(C 2—C 6)- and hydroxycarboxylic acids were prepared by reation with N,N′-dicyclohexyl-O-benzylisourea or with phenyldiazomethane. The hydroxycarboxylic acids lactic and 3-hydroxybutyric acid were also alkylated witn N,N′-dicyclohexyl-O-benzylisourea to give the correspondin O-benzyl ethers. The 2-oxocarboxylic acids pyruvic, oxaloacetic and 2-oxoglutaric acid were converted by means of O-benzylhydroxylamine hydrochloride into the corresponding O- benzyl oximes prior to esterification with phenyldiazomethane. The carboxylic acid benzyl esters were separated by gas chromatography on an SE-30 column. Mass spectra of the compounds were recorded with a MAT 111 GC—MS system. The main fragments at m/e 91 and m/e 107, found in all mass spectra, were de to the benzyl alcohol moiety of the esters. The general fragmentation pattern was similar to that of fatty acid and aromatic acid benzyl esters. The fragmentation scheme for this class of substances is discussed.

Specific chemical synthesis of ribonucleoside O-benzyl ethers.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSpecific chemical synthesis of ribonucleoside O-benzyl ethersLeon F. Christensen and Arthur D. BroomCite this: J. Org. Chem. 1972, 37, 22, 3398–3401Publication Date (Print):November 1, 1972Publication History Published online1 May 2002Published inissue 1 November 1972https://doi.org/10.1021/jo00795a003RIGHTS & PERMISSIONSArticle Views275Altmetric-Citations47LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (540 KB) Get e-Alerts Get e-Alerts