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Synthesis and kinetic analysis of the N-acetylhexosaminidase inhibitor XylNAc-isofagomine

TitleSynthesis and kinetic analysis of the N-acetylhexosaminidase inhibitor XylNAc-isofagomine
Publication TypeJournal Article
Year of Publication2005
AuthorsKnapp, S, Yang, CH, Pabbaraja, S, Rempel, B, Reid, S, Withers, SG
JournalJOURNAL OF ORGANIC CHEMISTRY
Volume70
Pagination7715-7720
Date PublishedSEP 16
ISSN0022-3263
Abstract

An efficient 10-step preparation from 4-methoxypyridine of (2R,3R,4R)-2-acetamido-3,4-dihydroxypiperidine ({''}XyINAe-isofagomine{''}) in optically active form is described. Key steps include an enantioselective reduction with catecholborane/(S)-2-methyl-CBS-oxazaborolidine, and a stereo-selective pseudo-glycosylation of lithium azide by a cyclic sulfite ester. The title compound showed a K-i = 21 mu M when evaluated against the N-acetyl-beta-hexosaminidase from Streptomyces plicatus.

DOI10.1021/jo051117e