Bismuth(III) Triflate-Catalyzed Dehydrative Glycosidation Using 1- Hydroxy Sugars

Takashi      Yamanoi; Ryo      Inoue; Sho      Matsuda; Keita      Hamasaki

doi:10.2174/157017808783330289

Abstract

This paper describes the O-glycoside formation from 1-hydroxy sugars by the bismuth(III) triflate-catalyzed dehydrative glycosidation. The reactions of the 1-hydroxy sugars with some primary alcohols in the presence of only 5 mol% bismuth(III) triflate at reflux for 15 min in dichloromethane afforded the O-glycosides in good yields. This paper clarifies several important properties during the bismuth(III) triflate-catalyzed dehydrative glycosidation using 1-hydroxy sugars.

Keywords: Glycosidation, bismuth(III) triflate, 1-hydroxy sugar, glycoside, 1,1'-disaccharide

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Letters in Organic Chemistry

Title: Bismuth(III) Triflate-Catalyzed Dehydrative Glycosidation Using 1- Hydroxy Sugars

Volume: 5 Issue: 1

Author(s): Takashi Yamanoi, Ryo Inoue, Sho Matsuda and Keita Hamasaki

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Keywords: Glycosidation, bismuth(III) triflate, 1-hydroxy sugar, glycoside, 1,1'-disaccharide

Abstract: This paper describes the O-glycoside formation from 1-hydroxy sugars by the bismuth(III) triflate-catalyzed dehydrative glycosidation. The reactions of the 1-hydroxy sugars with some primary alcohols in the presence of only 5 mol% bismuth(III) triflate at reflux for 15 min in dichloromethane afforded the O-glycosides in good yields. This paper clarifies several important properties during the bismuth(III) triflate-catalyzed dehydrative glycosidation using 1-hydroxy sugars.

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Yamanoi Takashi, Inoue Ryo, Matsuda Sho and Hamasaki Keita, Bismuth(III) Triflate-Catalyzed Dehydrative Glycosidation Using 1- Hydroxy Sugars, Letters in Organic Chemistry 2008; 5 (1) . https://dx.doi.org/10.2174/157017808783330289