Synthesis of ether-linked sugar by nucleophilic opening of carbohydrate oxiranes

Kazusa Nishiyama, Takahiro Nakayama, Hideaki Natsugari, Hideyo Takahashi

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5 Citations (Scopus)

Abstract

A new synthesis of ether-linked sugar utilizing the nucleophilic ring-opening reaction of carbohydrate α- or β-oxirane was developed. The reaction of 2,3-anhydro-α-D-mannopyranosides resulted in the expected high regioselectivity. In contrast, 2,3-anhydro-α-D-allopyranosides showed an unusual regioselectivity shift. The differentiating properties of carbohydrate α- or β-oxirane were investigated by comparing various conditions of the reaction.

Original languageEnglish
Article numberF15808SS
Pages (from-to)3761-3768
Number of pages8
JournalSynthesis
Issue number23
DOIs
Publication statusPublished - 1 Dec 2008

Keywords

  • Carbohydrates
  • Epoxides
  • Ethers
  • Regio-selectivity
  • Ring opening

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