Glycosyl 6-nitro-2-benzothiazoate. A highly efficient donor for β-stereoselective glycosylation

Teruaki Mukaiyama, Takashi Hashihayata, Hiroki Mandai

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Highly β-stereoselective glycosylations of glycosyl acceptors having a primary hydroxyl group by using a novel glycosyl donor, α-glycosyl 6-nitro-2-benzothiazoate (3), proceeded smoothly in the presence of a catalytic amount of trifluoromethanesulfonic acid (TfOH) in CH2Cl2 at -78°C to afford the corresponding glycosides in high yields. The donor 3 gave β-saccharides more dominantly compared with those using other α-glycosyl donors such as thioform- and trichloroacet-imidates or fluoride under the same conditions.

Original languageEnglish
Pages (from-to)340-341
Number of pages2
JournalChemistry Letters
Volume32
Issue number4
Publication statusPublished - Apr 5 2003
Externally publishedYes

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Imidoesters
Glycosylation
Glycosides
Fluorides
Hydroxyl Radical
trifluoromethanesulfonic acid

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Glycosyl 6-nitro-2-benzothiazoate. A highly efficient donor for β-stereoselective glycosylation. / Mukaiyama, Teruaki; Hashihayata, Takashi; Mandai, Hiroki.

In: Chemistry Letters, Vol. 32, No. 4, 05.04.2003, p. 340-341.

Research output: Contribution to journalArticle

Mukaiyama, Teruaki ; Hashihayata, Takashi ; Mandai, Hiroki. / Glycosyl 6-nitro-2-benzothiazoate. A highly efficient donor for β-stereoselective glycosylation. In: Chemistry Letters. 2003 ; Vol. 32, No. 4. pp. 340-341.
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