Glycosyl-Acceptor-Derived Borinic Ester-Promoted Direct and β-Stereoselective Mannosylation with a 1,2-Anhydromannose Donor

Masamichi Tanaka; Junki Nashida; Daisuke Takahashi; Kazunobu Toshima

doi:10.1021/acs.orglett.6b00926

Glycosyl-Acceptor-Derived Borinic Ester-Promoted Direct and β-Stereoselective Mannosylation with a 1,2-Anhydromannose Donor

Masamichi Tanaka, Junki Nashida, Daisuke Takahashi, Kazunobu Toshima

Department of Applied Chemistry

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

55 Citations (Scopus)

Abstract

β-Stereoselective mannosylations were conducted using a 1,2-anhydromannose 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 β-mannosides with high stereoselectivity in moderate to high yields. In addition, the present glycosylation method was applied successfully to the total synthesis of acremomannolipin A.

Original language	English
Pages (from-to)	2288-2291
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.6b00926
Publication status	Published - 2016 May 6

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Glycosyl-Acceptor-Derived Borinic Ester-Promoted Direct and β-Stereoselective Mannosylation with a 1,2-Anhydromannose Donor",

abstract = "β-Stereoselective mannosylations were conducted using a 1,2-anhydromannose 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 β-mannosides with high stereoselectivity in moderate to high yields. In addition, the present glycosylation method was applied successfully to the total synthesis of acremomannolipin A.",

author = "Masamichi Tanaka and Junki Nashida and Daisuke Takahashi 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, from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT). Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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doi = "10.1021/acs.orglett.6b00926",

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T1 - Glycosyl-Acceptor-Derived Borinic Ester-Promoted Direct and β-Stereoselective Mannosylation with a 1,2-Anhydromannose Donor

AU - Tanaka, Masamichi

AU - Nashida, Junki

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, from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT). Publisher Copyright: © 2016 American Chemical Society.

PY - 2016/5/6

Y1 - 2016/5/6

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AB - β-Stereoselective mannosylations were conducted using a 1,2-anhydromannose 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 β-mannosides with high stereoselectivity in moderate to high yields. In addition, the present glycosylation method was applied successfully to the total synthesis of acremomannolipin A.

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Glycosyl-Acceptor-Derived Borinic Ester-Promoted Direct and β-Stereoselective Mannosylation with a 1,2-Anhydromannose Donor

Abstract

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