6-Nitro-2-benzothiazolyl α-Glucoside and α-Mannoside in β-Selective Glycosylations

Takashi Hashihayata, Hiroki Mandai, Teruaki Mukaiyama

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Highly β-selective glucosylations of glycosyl acceptors having α primary hydroxy group with a 6-nitro-2-benzothia-zolyl α-glucoside donor 3α proceeded smoothly in the presence of a catalytic amount of trifluoromethanesulfonic acid (TfOH) in CH 2Cl2 at -78 °C to afford the corresponding glycosides in high yields. With the use of 3α, β-saccharides could be obtained more dominantly than other α-glucosyl donors such as thioform- and trichloroacet-imidates or fluoride in the glucosylation under the same conditions. Similarly, highly β-selective mannosylations of glycosyl acceptors with a 6-nitro-2-benzothiazolyl α-mannoside donor 18α were carried out smoothly in the presence of a catalytic amount of tetrakis(pentafluorophenyl)boric acid H[B(C6F5) 4] to afford the corresponding disaccharides in good to high yields; 18α apparently behaved as a potent donor here for the construction of β-mannoside linkage. Interestingly, in situ anomerization from 18β to 18α was observed when β-mannosyl donor 18β was treated with a catalytic amount of H[B(C6F5)4] in CH 2Cl2.

Original languageEnglish
Pages (from-to)169-178
Number of pages10
JournalBulletin of the Chemical Society of Japan
Volume77
Issue number1
DOIs
Publication statusPublished - 2004
Externally publishedYes

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Mannosides
Glycosylation
Glucosides
Imidoesters
Disaccharides
Glycosides
Fluorides
trifluoromethanesulfonic acid
boric acid

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

6-Nitro-2-benzothiazolyl α-Glucoside and α-Mannoside in β-Selective Glycosylations. / Hashihayata, Takashi; Mandai, Hiroki; Mukaiyama, Teruaki.

In: Bulletin of the Chemical Society of Japan, Vol. 77, No. 1, 2004, p. 169-178.

Research output: Contribution to journalArticle

Hashihayata, Takashi ; Mandai, Hiroki ; Mukaiyama, Teruaki. / 6-Nitro-2-benzothiazolyl α-Glucoside and α-Mannoside in β-Selective Glycosylations. In: Bulletin of the Chemical Society of Japan. 2004 ; Vol. 77, No. 1. pp. 169-178.
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