Journal of Carbohydrate Chemistry

N-Bromosuccinimide-Mediated Conversion of Allyl Glycosides to Glycosyl Hemiacetals

R Panchadhayee, AK Misra

Index: Panchadhayee, Rajib; Misra, Anup Kumar Journal of Carbohydrate Chemistry, 2010 , vol. 29, # 2 p. 76 - 83

Full Text: HTML

Citation Number: 5

Abstract

A novel reaction condition has been developed for the hydrolysis of differentially functionalized allyl glycosides to their corresponding glycosyl hemiacetal derivatives in the presence of N-bromosuccinimide (NBS). The reaction condition is exceptionally fast, mild, and compatible with most of the functional groups used in the oligosaccharide synthesis, and yields were excellent.

Related Articles:

Preparation and characterization of branched β-cyclodextrins having α-L-fucopyranose and a study of their functions

[Nishi, Yuki; Tanimoto, Toshiko Bioscience, Biotechnology and Biochemistry, 2009 , vol. 73, # 3 p. 562 - 569]

Glycosyl phosphites as glycosylation reagents: scope and mechanism

[Kondo, Hirosato; Aoki, Shin; Ichikawa, Yoshitaka; Halcomb, Randall L.; Ritzen, Helena; Wong, Chi-Huey Journal of Organic Chemistry, 1994 , vol. 59, # 4 p. 864 - 877]

New method for regioselective glycosylation employing saccharide oxyanions

[Matwiejuk, Martin; Thiem, Joachim European Journal of Organic Chemistry, 2011 , # 29 p. 5860 - 5878]

Chloramine-T-mediated chemoselective hydrolysis of thioglycosides into glycosyl hemiacetals under neutral conditions

[Misra, Anup Kumar; Agnihotri, Geetanjali Carbohydrate Research, 2004 , vol. 339, # 4 p. 885 - 890]

Glycosyl phosphites as glycosylation reagents: scope and mechanism

[Kondo, Hirosato; Aoki, Shin; Ichikawa, Yoshitaka; Halcomb, Randall L.; Ritzen, Helena; Wong, Chi-Huey Journal of Organic Chemistry, 1994 , vol. 59, # 4 p. 864 - 877]

More Articles...