The synthesis of a diastereoisomer of methyl acarviosin

Joseph C. McAuliffe, Robert V. Stick, D. Mathew G. Tilbrook, Andrew G. Watts

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

In model studies, a fully protected D-galactopyranoside 4-triflate and two 6-deoxy analogues were shown to alkylate cyclohexylamine, leading to 4-cyclohexylamino-4-deoxy- and 4,6-dideoxy-D-glucopyranosides as the major products in satisfactory yield, accompanied by alkenes resulting from elimination of triflic acid. Coupling of tetra-O-benzyl-l-epivalienamine with methyl 3- O-benzoyl-6-deoxy-4-O-trifluoromethylsulfonyl-β-D-galactoside gave a diastereoisomer of methyl acarviosin in protected form. Deprotection completed the first synthesis of methyl 4,6-dideoxy-4-[(l′R,4′R,5′ S,6′S)-4′,5′,6′-trihydroxy3′-(hydroxymethyl) cyclohex-2′-enyl]amino-β-D-glucoside, a potential β-glycosidase inhibitor.

Original languageEnglish
Pages (from-to)91-96
Number of pages6
JournalAustralian Journal of Chemistry
Volume51
Issue number2
DOIs
Publication statusPublished - 1 Jan 1998

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'The synthesis of a diastereoisomer of methyl acarviosin'. Together they form a unique fingerprint.

  • Cite this