Highly Stereoselective Introduction of Fluorine-Containing Methyl Groups at 2 Position of D-Glucose

Shuichi Hiraoka; Takashi Yamazaki; Tomoya Kitazume

doi:10.1055/s-1997-3264

Synlett 1997; 1997(6): 669-670
DOI: 10.1055/s-1997-3264

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Highly Stereoselective Introduction of Fluorine-Containing Methyl Groups at 2 Position of D-Glucose

Shuichi Hiraoka, Takashi Yamazaki^* , Tomoya Kitazume

^*Department of Bioengineering, Tokyo Institute of Technology, Nagatsuta-cho, Midori-ku, Yokohama 226, Japan

Abstract

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Highly stereoselective introduction of fluorine-containing methyl groups at the 2 position of methyl glucoside was attained by use of the difluoromethylene derivative as a key intermediate via hydrogenation of exo- and endo-olefins, whose diastereofacial selectivity was considered to be governed by the anomeric methoxy group.

fluorine-containing methyl groups - difluoromethylene carbohydrate

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