Synthesis of trehalose mimics by bismuth(III) triflate or bis(trifluoromethane)sulfonimide-catalyzed 1-C-methyl-d-hexopyranosylation

Takashi Yamanoi, Ryo Inoue, Sho Matsuda, Kaname Katsuraya, Keita Hamasaki

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

We investigated the ketopyranosylation of 2,3,4,6-tetra-O-benzyl-1-C-methyl-d-hexopyranoses with the benzylated d-aldohexopyranoses in order to produce novel non-reducing disaccharides as trehalose mimics. It was found that 5 mol % of bismuth(III) triflate or bis(trifluoromethane)sulfonimide efficiently catalyzed the ketopyranosylation that produced various non-reducing disaccharides.

Original languageEnglish
Pages (from-to)2914-2918
Number of pages5
JournalTetrahedron Asymmetry
Volume17
Issue number20
DOIs
Publication statusPublished - 2006 Nov 6

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Bismuth
Trehalose
Disaccharides
bismuth
synthesis
fluoroform

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Synthesis of trehalose mimics by bismuth(III) triflate or bis(trifluoromethane)sulfonimide-catalyzed 1-C-methyl-d-hexopyranosylation. / Yamanoi, Takashi; Inoue, Ryo; Matsuda, Sho; Katsuraya, Kaname; Hamasaki, Keita.

In: Tetrahedron Asymmetry, Vol. 17, No. 20, 06.11.2006, p. 2914-2918.

Research output: Contribution to journalArticle

Yamanoi, Takashi ; Inoue, Ryo ; Matsuda, Sho ; Katsuraya, Kaname ; Hamasaki, Keita. / Synthesis of trehalose mimics by bismuth(III) triflate or bis(trifluoromethane)sulfonimide-catalyzed 1-C-methyl-d-hexopyranosylation. In: Tetrahedron Asymmetry. 2006 ; Vol. 17, No. 20. pp. 2914-2918.
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