Direct Transformation of O-Glycoside into Glyosyl Bromide with the Combination of Trimethylsilyl Bromide and Zinc Bromide

Kunio HIGASHI; Kiyoshi NAKAYAMA; Emiko SHIOYA; Tsuneo KUSAMA

doi:10.1248/cpb.39.2502

Kunio HIGASHI, Kiyoshi NAKAYAMA, Emiko SHIOYA, Tsuneo KUSAMA

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Keywords: glycosyl bromide, trimethylsilyl bromide, zinc bromide, glucosamine, glucose, galactose, mannose, O-glycoside

JOURNAL FREE ACCESS

1991 Volume 39 Issue 10 Pages 2502-2504

DOI https://doi.org/10.1248/cpb.39.2502

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Abstract

A novel direct transformation of O-glycoside into glycosyl bromide by using trimethylsilyl bromide and zinc bromide has been developed. Treatment of various glycosides (3a-5a, 10, 12 and 14) with trimethylsilyl bromide and zinc bromide in dichloromethane afforded the glycosyl bromides (6, 11, 13 and 15) in 53, 85, 94, 47, 41 and 40% yields, respectively.

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