Recent advances in boron-mediated aglycon delivery (BMAD) for the efficient synthesis of 1,2-cis glycosides

Daisuke Takahashi; Kazuki Inaba; Kazunobu Toshima

doi:10.1016/j.carres.2022.108579

Recent advances in boron-mediated aglycon delivery (BMAD) for the efficient synthesis of 1,2-cis glycosides

Daisuke Takahashi, Kazuki Inaba, Kazunobu Toshima

Department of Applied Chemistry

Research output: Contribution to journal › Short survey › peer-review

2 Citations (Scopus)

Abstract

Highly stereoselective synthesis of 1,2-cis glycosides remains a challenging task due to the lack of reliable neighboring group participation (NGP) from the 2-O-acyl functionality in the glycosyl donor. In this context, our group recently developed highly 1,2-cis-stereoselective glycosylation methods, named boron-mediated aglycon delivery (BMAD), using organoboron reagents and 1,2-anhydroglycosyl donors. In this mini-review article, we introduce the BMAD methods and their applications to the synthesis of biologically active natural products and complex glycosides reported since our mini-review article published in this journal in 2017.

Original language	English
Article number	108579
Journal	Carbohydrate Research
Volume	518
DOIs	https://doi.org/10.1016/j.carres.2022.108579
Publication status	Published - 2022 Aug

Keywords

1,2-cis glycoside
Boron-mediated aglycon delivery
Glycosylation
Natural products
Regioselective
Stereoselective

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/j.carres.2022.108579

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title = "Recent advances in boron-mediated aglycon delivery (BMAD) for the efficient synthesis of 1,2-cis glycosides",

abstract = "Highly stereoselective synthesis of 1,2-cis glycosides remains a challenging task due to the lack of reliable neighboring group participation (NGP) from the 2-O-acyl functionality in the glycosyl donor. In this context, our group recently developed highly 1,2-cis-stereoselective glycosylation methods, named boron-mediated aglycon delivery (BMAD), using organoboron reagents and 1,2-anhydroglycosyl donors. In this mini-review article, we introduce the BMAD methods and their applications to the synthesis of biologically active natural products and complex glycosides reported since our mini-review article published in this journal in 2017.",

keywords = "1,2-cis glycoside, Boron-mediated aglycon delivery, Glycosylation, Natural products, Regioselective, Stereoselective",

author = "Daisuke Takahashi and Kazuki Inaba 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, JP16K05781 in Scientific Research (C), JP18J12129 in JSPS Fellows, JP19J13223 in JSPS Fellows, JP19H02724 in Scientific Research (B) and JP20K21289 in Challenging Research (Exploratory), a SUNBOR Grant from the Suntory Foundation for Life Sciences, and the Sasagawa Scientific Research Grant from the Japan Science Society . Publisher Copyright: {\textcopyright} 2022 Elsevier Ltd",

year = "2022",

month = aug,

doi = "10.1016/j.carres.2022.108579",

language = "English",

volume = "518",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier BV",

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TY - JOUR

T1 - Recent advances in boron-mediated aglycon delivery (BMAD) for the efficient synthesis of 1,2-cis glycosides

AU - Takahashi, Daisuke

AU - Inaba, Kazuki

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, JP16K05781 in Scientific Research (C), JP18J12129 in JSPS Fellows, JP19J13223 in JSPS Fellows, JP19H02724 in Scientific Research (B) and JP20K21289 in Challenging Research (Exploratory), a SUNBOR Grant from the Suntory Foundation for Life Sciences, and the Sasagawa Scientific Research Grant from the Japan Science Society . Publisher Copyright: © 2022 Elsevier Ltd

PY - 2022/8

Y1 - 2022/8

N2 - Highly stereoselective synthesis of 1,2-cis glycosides remains a challenging task due to the lack of reliable neighboring group participation (NGP) from the 2-O-acyl functionality in the glycosyl donor. In this context, our group recently developed highly 1,2-cis-stereoselective glycosylation methods, named boron-mediated aglycon delivery (BMAD), using organoboron reagents and 1,2-anhydroglycosyl donors. In this mini-review article, we introduce the BMAD methods and their applications to the synthesis of biologically active natural products and complex glycosides reported since our mini-review article published in this journal in 2017.

AB - Highly stereoselective synthesis of 1,2-cis glycosides remains a challenging task due to the lack of reliable neighboring group participation (NGP) from the 2-O-acyl functionality in the glycosyl donor. In this context, our group recently developed highly 1,2-cis-stereoselective glycosylation methods, named boron-mediated aglycon delivery (BMAD), using organoboron reagents and 1,2-anhydroglycosyl donors. In this mini-review article, we introduce the BMAD methods and their applications to the synthesis of biologically active natural products and complex glycosides reported since our mini-review article published in this journal in 2017.

KW - 1,2-cis glycoside

KW - Boron-mediated aglycon delivery

KW - Glycosylation

KW - Natural products

KW - Regioselective

KW - Stereoselective

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Recent advances in boron-mediated aglycon delivery (BMAD) for the efficient synthesis of 1,2-cis glycosides

Abstract

Keywords

ASJC Scopus subject areas

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