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Communication | Special issue | Vol 97, No. 1, 2018, pp.170-177
Published online, 26th March, 2018
DOI: 10.3987/COM-18-S(T)35
A Synthetic Approach to Derive exo-Glucal Derivatives Through the Reaction of a1-C-Vinylated Glucopyranose Derivative with Phenols

Takashi Yamanoi,* Sho Matsuda, Junki Nakgawa, Mikio Watanabe, Yoshiki Oda, and Akihiro Yoshida

*Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan

Abstract

In this study, a synthetic approach to prepare exo-glucal derivatives through the reaction of a 1-C-vinylated glucopyranose derivative with phenols in the presence of an appropriate promoter has been investigated. The reaction between 2,3,4,6-tetra-O-benzyl-1-C-vinyl-α-D-glucopyranose and different phenols using 5 mol% Bi(OTf)3 produced the corresponding exo-glucal derivatives as major products along with spiro O-glucoside derivatives as minor products.