Document Type
Article
Keywords
glycan, glycosylation, oligosaccharides, sugars, synthesis
Abstract
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-O-picoloyl donors and reactive glycosyl acceptors via the H-bond-mediated aglycone delivery (HAD) pathway. In contrast, glycosidations of the altrosamine donor equipped with the 3-O-benzoyl group were poorly stereoselective.
Publication Date
9-26-2022
Publication Title
Frontiers in Chemistry
E-ISSN
22962646
Volume
10
Original Article Number
945779
Rights
CC BY
DOI
10.3389/fchem.2022.945779
Funding Number
GM GM111835
Funding Sponsor
National Institute of General Medical Sciences
Recommended Citation
Novakova, Mariya; Das, Anupama; Alex, Catherine; and Demchenko, Alexei V., "Synthesis and glycosidation of building blocks of D-altrosamine" (2022). Chemistry & Biochemistry Faculty Works. 103.
DOI: https://doi.org/10.3389/fchem.2022.945779
Available at:
https://irl.umsl.edu/chemistry-faculty/103