An efficient synthesis of the protected carbohydrate moiety of Brasilicardin A.

A synthesis of the protected carbohydrate moiety 2 of Brasilicardin A starting from l-rhamnose and d-glucosamine is described. The disaccharide was synthesized using a TMSOTf-mediated glycosylation of the 2-phthalimido-2-deoxyglucose donor 5 and the 3-hydroxyl group of the protected L-rhamnose derivative 4, which already bears the 3-hydroxybenzoate unit. The imidate 2 was coupled via TMSOTf-mediated glycosidation with cholesterol as a model aglycone followed by the selective cleavage of all the acetate groups to give the Brasilicardin A analogue 16.