Regioselective and 1,2-cis-α-Stereoselective Glycosylation Utilizing Glycosyl-Acceptor-Derived Boronic Ester Catalyst

Akira Nakagawa; Masamichi Tanaka; Shun Hanamura; Daisuke Takahashi; Kazunobu Toshima

doi:10.1002/anie.201504182

Regioselective and 1,2-cis-α-Stereoselective Glycosylation Utilizing Glycosyl-Acceptor-Derived Boronic Ester Catalyst

Akira Nakagawa, Masamichi Tanaka, Shun Hanamura, Daisuke Takahashi, Kazunobu Toshima

Department of Applied Chemistry

Research output: Contribution to journal › Article

48 Citations (Scopus)

Abstract

Regioselective and 1,2-cis-α-stereoselective glycosylations using 1α,2α-anhydro glycosyl donors and diol glycosyl acceptors in the presence of a glycosyl-acceptor-derived boronic ester catalyst. The reactions proceed smoothly to give the corresponding 1,2-cis-α-glycosides with high stereo- and regioselectivities in high yields without any further additives under mild reaction conditions. In addition, the present glycosylation method was successfully applied to the synthesis of an isoflavone glycoside.

Original language	English
Pages (from-to)	10935-10939
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	37
DOIs	https://doi.org/10.1002/anie.201504182
Publication status	Published - 2015 Sep 1

Keywords

boron
glycosylation
regioselectivity
stereoselectivity
synthetic methods

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201504182

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abstract = "Regioselective and 1,2-cis-α-stereoselective glycosylations using 1α,2α-anhydro glycosyl donors and diol glycosyl acceptors in the presence of a glycosyl-acceptor-derived boronic ester catalyst. The reactions proceed smoothly to give the corresponding 1,2-cis-α-glycosides with high stereo- and regioselectivities in high yields without any further additives under mild reaction conditions. In addition, the present glycosylation method was successfully applied to the synthesis of an isoflavone glycoside.",

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AU - Hanamura, Shun

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

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