Synthesis of carba-sugars from (-)-quinic acid

Authors
Carballido, M Castedo, L Gonzalez, C
Citation
M. Carballido et al., Synthesis of carba-sugars from (-)-quinic acid, TETRAHEDR L, 42(24), 2001, pp. 3973-3976
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
24
Year of publication
2001
Pages
3973 - 3976
Database
ISI
SICI code
0040-4039(20010611)42:24<3973:SOCF(A>2.0.ZU;2-5
Abstract
(1S,2R,3R,4S,5R)- (3a) and (1S,2S,3S,4S,5R)-1,2,3,4,5-pentahydroxy-1-hydrox ymethylcyclohexane (4a), (1R,2R,3R, 4S,5R)- (3b) and (1R,2S,3S,4S,5R)-1,2,3 ,4,5-pentahydroxycyclohexan-1-carboxylic acid (4b) are reported. The synthe ses exploit the diastereoselective oxidation of the 5,6-double bond of the quinic acid-derived lactone 2 with osmium tetroxide. (C) 2001 Elsevier Scie nce Ltd. All rights reserved.