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

Research output: Contribution to journalArticle

32 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 languageEnglish
Pages (from-to)2288-2291
Number of pages4
JournalOrganic Letters
Volume18
Issue number9
DOIs
Publication statusPublished - 2016 May 6

Fingerprint

Mannosides
Glycosylation
Stereoselectivity
esters
Esters
synthesis
acremomannolipin A

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Glycosyl-Acceptor-Derived Borinic Ester-Promoted Direct and β-Stereoselective Mannosylation with a 1,2-Anhydromannose Donor. / Tanaka, Masamichi; Nashida, Junki; Takahashi, Daisuke; Toshima, Kazunobu.

In: Organic Letters, Vol. 18, No. 9, 06.05.2016, p. 2288-2291.

Research output: Contribution to journalArticle

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