SYNTHETIC APPROACH TO KDO GLYCOSIDES VIA EXO-GLYCAL EPOXIDES AND RATIONALIZATION OF THE STEREOCHEMICAL OUTCOME

Authors
LAY L NICOTRA F PANZA L RUSSO G SELLO G
Citation
L. Lay et al., SYNTHETIC APPROACH TO KDO GLYCOSIDES VIA EXO-GLYCAL EPOXIDES AND RATIONALIZATION OF THE STEREOCHEMICAL OUTCOME, Journal of carbohydrate chemistry, 17(8), 1998, pp. 1269-1281
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology
Journal title
Journal of carbohydrate chemistry → ACNP
ISSN journal
07328303
Volume
17
Issue
8
Year of publication
1998
Pages
1269 - 1281
Database
ISI
SICI code
0732-8303(1998)17:8<1269:SATKGV>2.0.ZU;2-8
Abstract
The use of epoxides obtained by dimethyldioxirane epoxidation of y-4,5 :7,8-di-O-isopropylidene-D-manno-oct-1-enitol as glycosyl donors is de scribed. This method offers a simple and stereoselective access to pre cursors of Kdo glycosides. The stereochemical outcome of the reaction is rationalized by means of semiempirical calculations of the transiti on states leading to glycosides formation.