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Improved catalytic and stereoselective glycosylation with glycosyl N-trichloroacetylcarbamate: application to various 1-hydroxy sugars

Authors :
Toshiaki Sunazuka
Tatsuya Shirahata
Satoko Teruya
Nozomu Hirata
Jun-ichi Matsuo
Satoshi Ōmura
Nanao Akimoto
Taku Kurimoto
Eisuke Kaji
Source :
Carbohydrate Research. 345:740-749
Publication Year :
2010
Publisher :
Elsevier BV, 2010.

Abstract

Efficient catalytic and stereoselective glycosylation was achieved by activating a glycosyl N -trichloroacetylcarbamate with a catalytic amount of Lewis acid in the presence of a glycosyl acceptor and 5 Ǻ molecular sieves. Catalytic one-pot dehydrative glycosylation of a 1-hydroxy carbohydrate was achieved stereoselectively by reaction with trichloroacetyl isocyanate, followed by activation with a catalytic amount of activators.

Details

ISSN :
00086215
Volume :
345
Database :
OpenAIRE
Journal :
Carbohydrate Research
Accession number :
edsair.doi.dedup.....a06dd8e7678c034cb84dd01ebbde6665
Full Text :
https://doi.org/10.1016/j.carres.2010.01.011