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-O-picoloyl donors and reactive gly...

Descripción completa

Detalles Bibliográficos
Autores principales: Novakova, Mariya, Das, Anupama, Alex, Catherine, Demchenko, Alexei V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9548543/
https://www.ncbi.nlm.nih.gov/pubmed/36226114
http://dx.doi.org/10.3389/fchem.2022.945779
Descripción
Sumario: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.

Ejemplares similares