Synthesis of pseudo-trehaloses: [(1,2, 4 3,5)-2,3,4-trihydroxy-5-hydroxymethyl-1-cyclohexyl] d-glucopyranosides

Seiichiro Ogawa, Shigeki Yokoi, Noritaka Kimura, Yasushi Shibata, Noritaka Chida

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)


All the theoretically possible, foru diastereoisomeric pairs, α,α (2A and 2B), α,β (3A and 3B), β,α (4A and 4B), and β,β (5A and 5B), of pseudo-trehalose, composed of d-glucopyranose and pseudo-d- or l-glucopyranose, have been synthesised by coupling of the appropriately protected pseudo-α- (6) and -β-dl-glucopyranoses (9) with d-glucopyranose derivatives (10 and 11) in the presence of trimethylsilyl trifluoromethanesulfonate. Elucidation of the structures and absolute configurations of the pseudo-disaccharides was based on the 1H-n.m.r. spectra of their octa-acetates and the optical rotations. None of the pseudo-trehaloses inhibited trehalase.

Original languageEnglish
Pages (from-to)57-66
Number of pages10
JournalCarbohydrate Research
Issue numberC
Publication statusPublished - 1988 Oct 1

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry


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