A NEW SYNTHESIS OF D-GLYCOSIDURONATES FROM UNPROTECTED D-URONIC ACIDS

Authors
BERTHO JN FERRIERES V PLUSQUELLEC D
Citation
Jn. Bertho et al., A NEW SYNTHESIS OF D-GLYCOSIDURONATES FROM UNPROTECTED D-URONIC ACIDS, Journal of the Chemical Society, Chemical Communications, (13), 1995, pp. 1391-1393
Citations number
27
Categorie Soggetti
Chemistry
Journal title
Journal of the Chemical Society, Chemical Communications → ACNP
ISSN journal
00224936
Issue
13
Year of publication
1995
Pages
1391 - 1393
Database
ISI
SICI code
0022-4936(1995):13<1391:ANSODF>2.0.ZU;2-J
Abstract
O-Glycosidation of totally O-unprotected D-galacturonic acid 1 in THF provides alpha-pyranosides 4a when promoted with BF3.OEt(2) whereas be ta-furanosides 6 beta were obtained in the presence of FeCl3; when the same reaction is performed with D-glucuronic acid 2 or ''D-glucurone' ' 3, alkyl-D-glucofuranosidurono-6,3-lactones 7 are synthesized in exc ellent yields and high beta-selectivity.