Title: Synthesis of 1-deoxymannojirimycin analogues using N-tosyl and N-nosyl activated aziridines derived from 1-amino-1-deoxyglucitol
Authors: Mao, Hua ×
Joly, GJ
Peeters, K
Hoornaert, GJ
Compernolle, Frans #
Issue Date: Jan-2001
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:57 issue:32 pages:6955-6967
Abstract: 3,4;5,6-Diisopropylidene protected 1-amino-1-deoxy-D-glucitol was transformed into N-tosyl and N-nosyl activated aziridine intermediates, which underwent ring opening by reaction with various nucleophiles. The 5,6-diols resulting from selective hydrolysis of the terminal acetal group were subjected to (2-N -->6-OH) cyclisation using two different methods for activation of 6-OH. Final deprotection of the N-nosyl and 3,4-acetal group proceeded smoothly to afford 6-substituted analogues of 1-deoxymannojirimycin. (C) 2001 Elsevier Science Ltd. All rights reserved.
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
× corresponding author
# (joint) last author

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