Synthesis and glycosidation of building blocks of D-altrosamine

Presented herein is a streamlined synthesis of building blocks of a rare sugar D-altrosamine. Also investigated was the glycosylation of different glycosyl acceptors with differentially protected altrosamine donors. High facial stereoselectivity was achieved with 3- -picoloyl donors and reactive glycosyl acceptors the H-bond-mediated aglycone delivery (HAD) pathway. In contrast, glycosidations of the altrosamine donor equipped with the 3- -benzoyl group were poorly stereoselective.