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  • Title: Stereoselective synthesis of a model alpha-glycoside of the beta-D-ManNAcp-(1-->4)-d-Glc disaccharide starting from lactose, avoiding the beta-mannosaminylation step.
    Author: Attolino E, Bonaccorsi F, Catelani G, D'Andrea F.
    Journal: Carbohydr Res; 2008 Oct 13; 343(15):2545-56. PubMed ID: 18722596.
    Abstract:
    A model isopropyl alpha-glycoside of the beta-d-ManNAc-(1-->4)-d-Glc disaccharide has been prepared from lactose, avoiding the beta-mannosaminylation step. Three complementary approaches involving first the preparation and then the glycosidation of beta-thiophenyl donors of the protected disaccharides, (a) beta-d-ManNAc-(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 alpha-isopropyl glycoside to an amination with inversion in position 2' followed by an epimerization at C-4'.
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