A synthesis of 2,2,2-Trichloroethyl 2-Acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside

doi:10.1071/CH9772689

Paper

A synthesis of 2,2,2-Trichloroethyl 2-Acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside

Published Mar 21, 1978 · J. Mclaren, R. Stick, S. Webb

Australian Journal of Chemistry

Q3 SJR score

5

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0

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Abstract

The conversion of 2-acetamido-2-deoxy-D-glucose into 2-acetamido-3,4,6- tri-O-acetyl-2-deoxy-α-D-glucosyl chloride has been reinvestigated and the chloride transformed, with some modification of the literature method, into 2,2,2-trichloroethyl 2-acetamido-4,6-O-benzylidene-2- deoxy-β-D-glucoside. This compound has been converted into the title compound by the sequence acetylation, acid hydrolysis and selective acetylation. An efficient synthesis of benzyl 2,3-di-O-acetyl-β-D- galacto-pyranosideis reported and its unsuccessful selective acetylation contrasted with the above.

Study Snapshot

This study successfully synthesized 2,2,2-trichloroethyl 2-acetamido-3,6-di-O-acetyl-2-deoxy--D-glucopyranoside from 2-acetamido-3,4,6-tri-O-acetyl

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

A synthesis of 2,2,2-Trichloroethyl 2-Acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside

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References

Citations

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A series of arabinopyranosides and glucopyranosides show potential as competitive inhibitors of the Zn-metalloproteinase from Saccharomonospora canescens, with structures that fit the S1-subsite and protect the active site Zn2+.

O-benzylated oxazoline derivatives of 2-acetamido-2-deoxy-d-glucopyranose from 1-propenyl glycosides. synthesis of the propenyl glycosides and their direct cyclization

This study demonstrates a method for synthesizing 1-propenyl glycosides and their conversion into oxazolines, with a modified 0 S 2 conformation for these compounds.

The Reactions of Monosaccharides

Chemoselective reagents have made it easier and safer to perform functional group transformations within monosaccharides, leading to the synthesis of deoxy and amino deoxy sugars.

The Reactions of Monosacharides

The Barton-McCombie method is effective for deoxygenating secondary alcohols, making it a useful method for synthesis of deoxy and amino deoxy sugars.

The Stereoselective Dehydrative α-Glucosylation Using 6-O-Acetyl- and 6-O-p-Nitrobenzoyl-2,3,4-tri-O-benzyl-D-glucopyranoses

This study presents a method for stereoselectively synthesizing α-linked glucobiose derivatives using specific glucopyranoses and a ternary mixture in dichloromethane.