• Home
  • Search Results
  • Transglucosidation of methyl and ethyl D-glucopyranosides by alcoholysis.

Transglucosidation of methyl and ethyl D-glucopyranosides by alcoholysis.

Carbohydrate research (2002-03-14)
Per J Garegg, Karl-Jonas Johansson, Peter Konradsson, Bengt Lindberg, Zygmunt Trumpakaj
ABSTRACT

The transglucosidations of methyl 4-O-methyl-alpha- and -beta-D-glucopyranoside in ethanolic camphor-10-sulfonic acid, and of ethyl 4-O-methyl-alpha- and -beta-D-glucopyranoside in methanolic camphor-10-sulfonic acid, have been studied. Samples were removed at intervals and the proportions of the glucosides determined by GC of their acetates. The results show that the anomer with the inverted configuration predominates in the initially formed product (approximately 59-70%). This indicates that all the studied reactions proceed via the same mechanism, involving exocyclic C-O cleavage and formation of a glucopyranosylium ion, but that the eliminated alcohol exerts some steric hindrance, which favors the approach of the other alcohol from the opposite side.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(1S)-(+)-10-Camphorsulfonic acid, 99%
Sigma-Aldrich
(1R)-(−)-10-Camphorsulfonic acid, 98%
Sigma-Aldrich
Camphor-10-sulfonic acid (β), 98%
Sigma-Aldrich
(+)-Camphor-10-sulfonic acid, purum, ≥98.0% (T)
Sigma-Aldrich
(−)-Camphor-10-sulfonic acid, purum, ≥98.0% (T)

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.