Synthesis and glycosidase-inhibitory activity of cyclophellitol analogues

Vincent W.-F. Tai, P. H. Fung, Y. S. Wong, Tony K.M. Shing

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The 6-deoxy-1,2-anhydro-analogues of cyclophellitol, 5 and 6, have been synthesised from diol 11 via a regioselective ring opening of the cyclic sulfate 15, an internal SN2 reaction and hydrogenolysis. Compounds 5, 6, cyclophellitol 1 and its diastereoisomers 2-4 were assayed for inhibitory activity against six glycosidases. Oxirane 5 was shown to possess activity towards both β-mannosidase (A. oryzae) and β-glucosidase (almonds) but 6 showed no significant inhibitory activity.

Original languageEnglish
Pages (from-to)1353-1362
Number of pages10
JournalTetrahedron: Asymmetry
Volume5
Issue number7
DOIs
Publication statusPublished - 1994 Jul

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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