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

Authors :
Knapp, Spencer
Chunhua Yang
Pabbaraja, Srihari
Rempel, Brain
Reid, Steven
Withers, Sephen G.
Source :
Journal of Organic Chemistry. Sept 16, 2005, Vol. 70 Issue 19, p7715, 6 p.
Publication Year :
2005

Abstract

An efficient 10-step preparation from 4-methoxypyridine of (2R,3R,4R)-2-acetamido-3,4-dihydroxy-piperidine ('XylNAc-isofagomine') in optically active form is described. Key steps include an enantioselective reduction with cateholborane/(S)-2-methyl-CBS-oxazaborolidine, and a stereoselective pseudo-glycosylation of lithium azide by a cyclic sulfite ester.

Details

Language :
English
ISSN :
00223263
Volume :
70
Issue :
19
Database :
Gale General OneFile
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsgcl.140032486