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 journalArticle

16 Citations (Scopus)

Abstract

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
Volume181
Issue numberC
DOIs
Publication statusPublished - 1988 Oct 1

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Trehalose
Trehalase
Optical rotation
Optical Rotation
Disaccharides
Acetates
Derivatives
trimethylsilyl trifluoromethanesulfonate

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthesis of pseudo-trehaloses : [(1,2, 4 3,5)-2,3,4-trihydroxy-5-hydroxymethyl-1-cyclohexyl] d-glucopyranosides. / Ogawa, Seiichiro; Yokoi, Shigeki; Kimura, Noritaka; Shibata, Yasushi; Chida, Noritaka.

In: Carbohydrate Research, Vol. 181, No. C, 01.10.1988, p. 57-66.

Research output: Contribution to journalArticle

Ogawa, Seiichiro ; Yokoi, Shigeki ; Kimura, Noritaka ; Shibata, Yasushi ; Chida, Noritaka. / Synthesis of pseudo-trehaloses : [(1,2, 4 3,5)-2,3,4-trihydroxy-5-hydroxymethyl-1-cyclohexyl] d-glucopyranosides. In: Carbohydrate Research. 1988 ; Vol. 181, No. C. pp. 57-66.
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