Efficient generation of thiolate sugars from glycosyl Bunte salts and its application to S-glycoside synthesis

Yasuhiro Meguro; Masato Noguchi; Gefei Li; Shin ichiro Shoda

doi:10.1016/j.tetlet.2020.152198

Efficient generation of thiolate sugars from glycosyl Bunte salts and its application to S-glycoside synthesis

Yasuhiro Meguro, Masato Noguchi, Gefei Li, Shin ichiro Shoda

AGR - Agricultural Chemistry

Tohoku University

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

6 Citations (Scopus)

Abstract

A one-pot aqueous solution method for synthesis of S-glycoside derivatives has been developed. Firstly, unprotected sugars were converted into glycosyl Bunte salts from which thiolate sugars can be generated efficiently using Na₂S. The subsequent addition reaction with vinyl compounds or organic halides has successfully been demonstrated, giving rise to the corresponding S-glycosides.

Original language	English
Article number	152198
Journal	Tetrahedron Letters
Volume	61
Issue number	32
DOIs	https://doi.org/10.1016/j.tetlet.2020.152198
Publication status	Published - 2020 Aug 6

Keywords

Glycosyl Bunte salt
Glycosyl thiolate
One-pot aqueous synthesis
S-Glycoside
Sodium sulfide

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10.1016/j.tetlet.2020.152198

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title = "Efficient generation of thiolate sugars from glycosyl Bunte salts and its application to S-glycoside synthesis",

abstract = "A one-pot aqueous solution method for synthesis of S-glycoside derivatives has been developed. Firstly, unprotected sugars were converted into glycosyl Bunte salts from which thiolate sugars can be generated efficiently using Na2S. The subsequent addition reaction with vinyl compounds or organic halides has successfully been demonstrated, giving rise to the corresponding S-glycosides.",

keywords = "Glycosyl Bunte salt, Glycosyl thiolate, One-pot aqueous synthesis, S-Glycoside, Sodium sulfide",

author = "Yasuhiro Meguro and Masato Noguchi and Gefei Li and Shoda, {Shin ichiro}",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology , Japan. Publisher Copyright: {\textcopyright} 2020 Elsevier Ltd",

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AU - Meguro, Yasuhiro

AU - Noguchi, Masato

AU - Li, Gefei

AU - Shoda, Shin ichiro

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology , Japan. Publisher Copyright: © 2020 Elsevier Ltd

PY - 2020/8/6

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N2 - A one-pot aqueous solution method for synthesis of S-glycoside derivatives has been developed. Firstly, unprotected sugars were converted into glycosyl Bunte salts from which thiolate sugars can be generated efficiently using Na2S. The subsequent addition reaction with vinyl compounds or organic halides has successfully been demonstrated, giving rise to the corresponding S-glycosides.

AB - A one-pot aqueous solution method for synthesis of S-glycoside derivatives has been developed. Firstly, unprotected sugars were converted into glycosyl Bunte salts from which thiolate sugars can be generated efficiently using Na2S. The subsequent addition reaction with vinyl compounds or organic halides has successfully been demonstrated, giving rise to the corresponding S-glycosides.

KW - Glycosyl Bunte salt

KW - Glycosyl thiolate

KW - One-pot aqueous synthesis

KW - S-Glycoside

KW - Sodium sulfide

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Efficient generation of thiolate sugars from glycosyl Bunte salts and its application to S-glycoside synthesis

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Keywords

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