2-(Trimethylsilyl) ethyl glycosides. Transformation into glycopyranosyl chlorides

K Jansson, G Noori, G Magnusson

Index: Jansson, Karl; Noori, Ghazi; Magnusson, Goeran Journal of Organic Chemistry, 1990 , vol. 55, # 10 p. 3181 - 3185

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Citation Number: 83

Abstract

2-(Trimethylsily1) ethyl (TMSET) glycosides were transformed in high yields into the corresponding 1-chloro sugars by treatment with 1, l-dichloromethyl methyl ether/zinc chloride. With acetyl, benzoyl, and benzyl protection of the 2-position, the a-glycopyranosyl chloride was the major product, whereas with the 2-phthalimido sugar 13, the@-chloride 21 was obtained. The fully benzylated TMSET glucopyranoside 1 gave the a-chloro sugar 22 ...