Carbohydrate Research 2010-04-19

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

Tatsuya Shirahata, Jun-ichi Matsuo, Satoko Teruya, Nozomu Hirata, Taku Kurimoto, Nanao Akimoto, Toshiaki Sunazuka, Eisuke Kaji, Satoshi Omura

Index: Carbohydr. Res. 345(6) , 740-9, (2010)

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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 5A 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.Copyright (c) 2010 Elsevier Ltd. All rights reserved.