Nouvelle Synthese de L'Acide 3-Desoxy-D-Erythro-2-Hexulosonique (KDG). A Partir De La D-Glucono-1,5-Lactone Synthese Et Etude De RMN De Derives O-Methyles Du KDG
Title:
Nouvelle Synthese de L'Acide 3-Desoxy-D-Erythro-2-Hexulosonique (KDG). A Partir De La D-Glucono-1,5-Lactone Synthese Et Etude De RMN De Derives O-Methyles Du KDG
Author:
Plantier-Royon, Richard Cardona, Frederic Anker, Daniel Condemine, Guy Nasser, William Robert-Baudouy, Janine
Appeared in:
Journal of carbohydrate chemistry
Paging:
Volume 10 (1991) nr. 5 pages 787-811
Year:
1991
Contents:
3-Deoxy-D-erythro-2-hexulosonic acid (KDG), an important metabolite of bacterial polysaccharide degradation, was prepared from D-glucono-1,5-lactone through a six-step sequence, with a 45% overall yield. Using suitable intermediates. KDG methyl ester and its 5- and 6-O-methylated derivatives were also synthesized. 1H and 13C NMR studies of 5- and 6-O-methylated derivatives (pyranoid and furanoid forms respectively) compared to those of KDG and its methyl ester allowed us to conclude that these two latter compounds exist in equilibrium as forms whose percentages were determined.