Substituent effects in endocyclic cleavage-recyclization anomerization reaction of pyranosides

Shino Manabe, Kazuyuki Ishii, Hiroko Satoh, Yukishige Ito

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

Pyranosides with 2,3-trans carbamate or 2,3-trans carbonate groups are anomerized under mild acidic conditions via endocyclic cleavage reaction. In order to understand the nature of the anomerization reaction via the endocyclic cleavage-recyclization process, the substituent effects at various positions were investigated.

Original languageEnglish
Pages (from-to)9966-9974
Number of pages9
JournalTetrahedron
Volume67
Issue number51
DOIs
Publication statusPublished - 2011 Dec 23
Externally publishedYes

Keywords

  • Anomerization
  • Carbohydrate
  • Endocyclic cleavage
  • Substituent effect

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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