1,2-cis-α-Stereoselective Glycosylation Utilizing a Glycosyl-Acceptor-Derived Borinic Ester and Its Application to the Total Synthesis of Natural Glycosphingolipids

Masamichi Tanaka; Daisuke Takahashi; Kazunobu Toshima

doi:10.1021/acs.orglett.6b02488

1,2-cis-α-Stereoselective Glycosylation Utilizing a Glycosyl-Acceptor-Derived Borinic Ester and Its Application to the Total Synthesis of Natural Glycosphingolipids

Masamichi Tanaka, Daisuke Takahashi, Kazunobu Toshima

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

39 Citations (Scopus)

Abstract

1,2-cis-α-Stereoselective glycosylations were conducted using a 1,2-anhydroglucose donor and mono-ol acceptors in the presence of a glycosyl-acceptor-derived borinic ester. Reactions proceeded smoothly under mild conditions to provide the corresponding α-glycosides with high stereoselectivity in moderate to high yields. In addition, the present method was applied successfully to the direct glycosylation of a protected ceramide acceptor and the total synthesis of natural glycosphingolipids (GSLs).

Original language	English
Pages (from-to)	5030-5033
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.6b02488
Publication status	Published - 2016 Oct 7

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "1,2-cis-α-Stereoselective glycosylations were conducted using a 1,2-anhydroglucose donor and mono-ol acceptors in the presence of a glycosyl-acceptor-derived borinic ester. Reactions proceeded smoothly under mild conditions to provide the corresponding α-glycosides with high stereoselectivity in moderate to high yields. In addition, the present method was applied successfully to the direct glycosylation of a protected ceramide acceptor and the total synthesis of natural glycosphingolipids (GSLs).",

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AU - Tanaka, Masamichi

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

N1 - Funding Information: This research was supported in part by the MEXT-supported Program for the Strategic Research Foundation at Private Universities, 2012-2016, and JSPS KAKENHI Grant Numbers JP16H01161 in Middle Molecular Strategy and JP16K05781. Publisher Copyright: © 2016 American Chemical Society.

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1,2-cis-α-Stereoselective Glycosylation Utilizing a Glycosyl-Acceptor-Derived Borinic Ester and Its Application to the Total Synthesis of Natural Glycosphingolipids

Abstract

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