AUTHOR=Novakova Mariya , Das Anupama , Alex Catherine , Demchenko Alexei V. 

TITLE=Synthesis and glycosidation of building blocks of D-altrosamine

JOURNAL=Frontiers in Chemistry

VOLUME=10

YEAR=2022

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2022.945779

DOI=10.3389/fchem.2022.945779

ISSN=2296-2646

ABSTRACT=<p>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-<italic>O</italic>-picoloyl donors and reactive glycosyl acceptors <italic>via</italic> the H-bond-mediated aglycone delivery (HAD) pathway. In contrast, glycosidations of the altrosamine donor equipped with the 3-<italic>O</italic>-benzoyl group were poorly stereoselective.</p>