Novel 1,2-cis-stereoselective glycosylations utilizing organoboron reagents and their application to natural products and complex oligosaccharide synthesis

Daisuke Takahashi; Masamichi Tanaka; Nobuya Nishi; Kazunobu Toshima

doi:10.1016/j.carres.2017.10.004

Novel 1,2-cis-stereoselective glycosylations utilizing organoboron reagents and their application to natural products and complex oligosaccharide synthesis

Daisuke Takahashi, Masamichi Tanaka, Nobuya Nishi, Kazunobu Toshima

Department of Applied Chemistry

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

27 Citations (Scopus)

Abstract

In this mini-review article, 1,2-cis-stereoselective glycosylation methods utilizing organoboron reagents and 1,2-anhydroglycosyl donors that were developed in our laboratory, including regio- and 1,2-cis-stereoselective glycosylations using glycosyl-acceptor-derived boronic ester catalysts and 1,2-cis-stereoselective glycosylations using glycosyl-acceptor-derived borinic ester catalysts, are recounted. Representative applications of these methods to the synthesis of biologically active natural products and a complex oligosaccharide are also described.

Original language	English
Pages (from-to)	64-77
Number of pages	14
Journal	Carbohydrate Research
Volume	452
DOIs	https://doi.org/10.1016/j.carres.2017.10.004
Publication status	Published - 2017 Nov 27

Keywords

1,2-cis-Glycoside
Borinic acid
Boronic acid
Glycosylation
Regioselective
Stereoselective

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/j.carres.2017.10.004

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title = "Novel 1,2-cis-stereoselective glycosylations utilizing organoboron reagents and their application to natural products and complex oligosaccharide synthesis",

abstract = "In this mini-review article, 1,2-cis-stereoselective glycosylation methods utilizing organoboron reagents and 1,2-anhydroglycosyl donors that were developed in our laboratory, including regio- and 1,2-cis-stereoselective glycosylations using glycosyl-acceptor-derived boronic ester catalysts and 1,2-cis-stereoselective glycosylations using glycosyl-acceptor-derived borinic ester catalysts, are recounted. Representative applications of these methods to the synthesis of biologically active natural products and a complex oligosaccharide are also described.",

keywords = "1,2-cis-Glycoside, Borinic acid, Boronic acid, Glycosylation, Regioselective, Stereoselective",

author = "Daisuke Takahashi and Masamichi Tanaka and Nobuya Nishi and Kazunobu Toshima",

note = "Funding Information: This research was supported in part by the MEXT -supported Program for the Strategic Research Foundation at Private Universities, 2012–2016 ( S1201020 ), and JSPS KAKENHI Grant Numbers JP16H01161 in Middle Molecular Strategy and JP16K05781 . Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

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doi = "10.1016/j.carres.2017.10.004",

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journal = "Carbohydrate Research",

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AU - Takahashi, Daisuke

AU - Tanaka, Masamichi

AU - Nishi, Nobuya

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 ( S1201020 ), and JSPS KAKENHI Grant Numbers JP16H01161 in Middle Molecular Strategy and JP16K05781 . Publisher Copyright: © 2017 Elsevier Ltd

PY - 2017/11/27

Y1 - 2017/11/27

N2 - In this mini-review article, 1,2-cis-stereoselective glycosylation methods utilizing organoboron reagents and 1,2-anhydroglycosyl donors that were developed in our laboratory, including regio- and 1,2-cis-stereoselective glycosylations using glycosyl-acceptor-derived boronic ester catalysts and 1,2-cis-stereoselective glycosylations using glycosyl-acceptor-derived borinic ester catalysts, are recounted. Representative applications of these methods to the synthesis of biologically active natural products and a complex oligosaccharide are also described.

AB - In this mini-review article, 1,2-cis-stereoselective glycosylation methods utilizing organoboron reagents and 1,2-anhydroglycosyl donors that were developed in our laboratory, including regio- and 1,2-cis-stereoselective glycosylations using glycosyl-acceptor-derived boronic ester catalysts and 1,2-cis-stereoselective glycosylations using glycosyl-acceptor-derived borinic ester catalysts, are recounted. Representative applications of these methods to the synthesis of biologically active natural products and a complex oligosaccharide are also described.

KW - 1,2-cis-Glycoside

KW - Borinic acid

KW - Boronic acid

KW - Glycosylation

KW - Regioselective

KW - Stereoselective

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AN - SCOPUS:85032025732

SN - 0008-6215

VL - 452

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JO - Carbohydrate Research

JF - Carbohydrate Research

ER -

Novel 1,2-cis-stereoselective glycosylations utilizing organoboron reagents and their application to natural products and complex oligosaccharide synthesis

Abstract

Keywords

ASJC Scopus subject areas

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