Comparing of endocyclic and exocyclic cleavage reactions using mycothiol synthesis as an example

Shino Manabe, Yukishige Ito

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Glycosides can be cleaved in either an exo- or endocyclic fashion. Specifically, the former pathway is used during conventional glycosylation; whereas the latter pathway has not been the subject of attention. Endocyclic cleavage reaction enable the anomerization of β-glycosides to α-glycosides. Herein, we compared the efficacies of endo- and exocyclic cleavage reactions during the synthesis of mycothiol, a potential drug development target for tuberculosis treatment, in terms of selectivity and product yield. In addition, the direct resolution of benzyl-protected inositol by a highly stereoselective glycosylation reaction was investigated.

Original languageEnglish
Pages (from-to)2440-2446
Number of pages7
JournalTetrahedron
Volume74
Issue number20
DOIs
Publication statusPublished - 2018 May 17
Externally publishedYes

Keywords

  • Anomerization
  • Cyclitols
  • Glycosides
  • Glycosylation
  • Mycothiol

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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