Synthesis of C-disaccharides via a hetero-Diels-Alder reaction and further stereocontrolled transformations.
The partial de novo synthesis of two new C-disaccharides containing D-glucosamine is described. The strategy is based on a hetero-Diels-Alder reaction leading to a 1:1 mixture of separable cycloadducts, which have been stereoselectively functionalized and converted into alpha-D-Galp-(1-->3)-C-D-GlcpNAc and alpha-l-Galp-(1-->3)-C-D-GlcpNAc.
Wan
Qian
Q
ICMMO Université Paris-Sud 11, Orsay Cedex, France.
Lubineau
André
A
Guillot
Régis
R
Scherrmann
Marie-Christine
MC
D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D004187:Disaccharides