Synthesis of carba-beta-D- and L-idopyranosides by rearrangement of unsaturated sugars

Authors
Sollogoub, M Pearce, AJ Herault, A Sinay, P
Citation
M. Sollogoub et al., Synthesis of carba-beta-D- and L-idopyranosides by rearrangement of unsaturated sugars, TETRAHEDR-A, 11(1), 2000, pp. 283-294
Citations number
29
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
1
Year of publication
2000
Pages
283 - 294
Database
ISI
SICI code
0957-4166(20000128)11:1<283:SOCALB>2.0.ZU;2-A
Abstract
The triisobutylaluminium- (TIBAL) and titanium(IV)-promoted conversions of 6-deoxyhex-5-enopyranosides into highly functionalised cyclohexane derivati ves provide intermediates for the synthesis of enantiomerically pure carba- sugars. The preparation of enantiomerically pure methyl carba-beta-D-idopyr anoside 1, methyl carba-beta-L-idopyranoside 2 and 5'a-carbadisaccharide 3 is reported. (C) 2000 Elsevier Science Ltd. All rights reserved.