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...

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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
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author Novakova, Mariya
Das, Anupama
Alex, Catherine
Demchenko, Alexei V.
author_facet Novakova, Mariya
Das, Anupama
Alex, Catherine
Demchenko, Alexei V.
author_sort Novakova, Mariya
collection PubMed
description 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.
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spelling pubmed-95485432022-10-11 Synthesis and glycosidation of building blocks of D-altrosamine Novakova, Mariya Das, Anupama Alex, Catherine Demchenko, Alexei V. Front Chem Chemistry 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. Frontiers Media S.A. 2022-09-26 /pmc/articles/PMC9548543/ /pubmed/36226114 http://dx.doi.org/10.3389/fchem.2022.945779 Text en Copyright © 2022 Novakova, Das, Alex and Demchenko. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Novakova, Mariya
Das, Anupama
Alex, Catherine
Demchenko, Alexei V.
Synthesis and glycosidation of building blocks of D-altrosamine
title Synthesis and glycosidation of building blocks of D-altrosamine
title_full Synthesis and glycosidation of building blocks of D-altrosamine
title_fullStr Synthesis and glycosidation of building blocks of D-altrosamine
title_full_unstemmed Synthesis and glycosidation of building blocks of D-altrosamine
title_short Synthesis and glycosidation of building blocks of D-altrosamine
title_sort synthesis and glycosidation of building blocks of d-altrosamine
topic Chemistry
url 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
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