Evidence for endocyclic cleavage of conformationally restricted glycopyranosides

Shino Manabe, Kazuyuki Ishii, Daisuke Hashizume, Hiroyuki Koshino, Yukishige Ito

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

2,3-trans-carbamate- and -carbonate-carrying pyranosides were very easily anomerised from the ß to the a direction in the presence of a Lewis acid compared to other pyranosides. This reaction is caused by endocyclic cleavage of the pyranosides. Evidence for endocyclic cleavage of conformationally restricted pyranosides in the chair form was obtained by intra- and intermolecular FriedelCrafts reactions, chloride addition, and reduction of the generated cation. On the other hand, pyranosides with the distorted conformation were never cleaved in an endocyclic manner.

Original languageEnglish
Pages (from-to)6894-6901
Number of pages8
JournalChemistry - A European Journal
Volume15
Issue number28
DOIs
Publication statusPublished - 2009 Jul 13
Externally publishedYes

Keywords

  • Carbohydrates
  • Cations
  • Cleavage reactions
  • Friedel-crafts reaction
  • Reduction

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Evidence for endocyclic cleavage of conformationally restricted glycopyranosides'. Together they form a unique fingerprint.

  • Cite this