Title: The synthesis of 6-azido and 6-amino analogues of 1-deoxynojirimycin and their conversion to bicyclic derivatives
Authors: Kilonda, Amuri ×
Compernolle, Frans
Peeters, Koen
Joly, GJ
Toppet, Suzanne
Hoornaert, GJ #
Issue Date: Jan-2000
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:56 issue:7 pages:1005-1012
Abstract: 1-Amino-1-deoxy-D-glucitol (14) was converted to the N-Boc-2,3;5,6-di-O-isopropylidene derivative 16 which was transformed further into the selectively protected 2,3-O-isopropylidene 6-azido piperidine 3. The synthesis proceeded via a double inversion at C-5 involving internal attack of 4-OH to form the 4,5-epoxide 28, and ring opening of this epoxide by 1-NH2 to generate the piperidine 3. This served as a valuable precursor of various target compounds, i.e. 6-azido- and 6-amino-1,6-dideoxynojirimycin 4 and 5, and the mono- and bicyclic derivatives 6-12. (C) 2000 Elsevier Science Ltd. All rights reserved.
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
Biomechanics Section
Chemistry - miscellaneous
× corresponding author
# (joint) last author

Files in This Item:

There are no files associated with this item.

Request a copy


All items in Lirias are protected by copyright, with all rights reserved.

© Web of science