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

応用化学科

研究成果: Article › 査読

39 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	64-77
ページ数	14
ジャーナル	Carbohydrate Research
巻	452
DOI	https://doi.org/10.1016/j.carres.2017.10.004
出版ステータス	Published - 2017 11月 27

ASJC Scopus subject areas

分析化学
生化学
有機化学

文献へのアクセス

10.1016/j.carres.2017.10.004

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引用スタイル

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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{\textendash}2016 ( S1201020 ), and JSPS KAKENHI Grant Numbers JP16H01161 in Middle Molecular Strategy and JP16K05781 . Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

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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

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KW - 1,2-cis-Glycoside

KW - Borinic acid

KW - Boronic acid

KW - Glycosylation

KW - Regioselective

KW - Stereoselective

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