A model isopropyl a-glycoside of the beta-D-ManNAc-(1→4)-D-Glc disaccharide has been prepared from lactose, avoiding the b-mannosaminylation step. Three complementary approaches involving first the preparation and then the glycosidation of beta-thiophenyl donors of the protected disaccharides, (a) beta-DManNAc-(1→4)-D-Glc, (b) beta-D-TalNAc-(1→4)-D-Glc and (c) lactose, were compared. The best results were obtained employing a suitably protected lactose donor, and submitting its a-isopropyl glycoside to an amination with inversion in position 2’ followed by an epimerization at C-4’ .
|Autori interni:||CATELANI, GIORGIO|
|Autori:||ATTOLINO E; BONACCORSI F; CATELANI G; DANDREA F|
|Titolo:||Stereoselective synthesis of a model alfa-glycoside of the beta-D-ManNAcp-(1-->4)-D-Glc disaccharide starting from lactose, avoiding the beta-mannosaminylation step|
|Anno del prodotto:||2008|
|Digital Object Identifier (DOI):||10.1016/j.carres.2008.07.006|
|Appare nelle tipologie:||1.1 Articolo in rivista|