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

研究成果: Article査読

17 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)57-66
ページ数10
ジャーナルCarbohydrate Research
181
C
DOI
出版ステータスPublished - 1988 10 1

ASJC Scopus subject areas

  • 分析化学
  • 生化学
  • 有機化学

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