A Direct Method for β-Selective Glycosylation with an N-Acetylglucosamine Donor Armed by a 4-O-TBDMS Protecting Group

A new direct method for β-selective glycosylation with an N-acetylglucosamine (GlcNAc) donor was developed. This substrate, which can be readily prepared from commercially available GlcNAc in two steps, contains a 4-O-tert-butyldimethylsilyl (TBDMS) protecting group as a key component. We found that...

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Detalles Bibliográficos
Autores principales: Tanaka, Hidenori, Hamaya, Yu, Kotsuki, Hiyoshizo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6155425/
https://www.ncbi.nlm.nih.gov/pubmed/28282905
http://dx.doi.org/10.3390/molecules22030429
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author Tanaka, Hidenori
Hamaya, Yu
Kotsuki, Hiyoshizo
author_facet Tanaka, Hidenori
Hamaya, Yu
Kotsuki, Hiyoshizo
author_sort Tanaka, Hidenori
collection PubMed
description A new direct method for β-selective glycosylation with an N-acetylglucosamine (GlcNAc) donor was developed. This substrate, which can be readily prepared from commercially available GlcNAc in two steps, contains a 4-O-tert-butyldimethylsilyl (TBDMS) protecting group as a key component. We found that this functionality could have a favorable effect on the reactivity of the GlcNAc donor. Glycosylation with the armed donor using primary alcohols in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf) in 1,2-dichloroethane smoothly gave the desired coupling products in good yields with complete β-selectivity, while sterically hindered acceptors were less efficient.
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spelling pubmed-61554252018-11-13 A Direct Method for β-Selective Glycosylation with an N-Acetylglucosamine Donor Armed by a 4-O-TBDMS Protecting Group Tanaka, Hidenori Hamaya, Yu Kotsuki, Hiyoshizo Molecules Communication A new direct method for β-selective glycosylation with an N-acetylglucosamine (GlcNAc) donor was developed. This substrate, which can be readily prepared from commercially available GlcNAc in two steps, contains a 4-O-tert-butyldimethylsilyl (TBDMS) protecting group as a key component. We found that this functionality could have a favorable effect on the reactivity of the GlcNAc donor. Glycosylation with the armed donor using primary alcohols in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf) in 1,2-dichloroethane smoothly gave the desired coupling products in good yields with complete β-selectivity, while sterically hindered acceptors were less efficient. MDPI 2017-03-08 /pmc/articles/PMC6155425/ /pubmed/28282905 http://dx.doi.org/10.3390/molecules22030429 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Tanaka, Hidenori
Hamaya, Yu
Kotsuki, Hiyoshizo
A Direct Method for β-Selective Glycosylation with an N-Acetylglucosamine Donor Armed by a 4-O-TBDMS Protecting Group
title A Direct Method for β-Selective Glycosylation with an N-Acetylglucosamine Donor Armed by a 4-O-TBDMS Protecting Group
title_full A Direct Method for β-Selective Glycosylation with an N-Acetylglucosamine Donor Armed by a 4-O-TBDMS Protecting Group
title_fullStr A Direct Method for β-Selective Glycosylation with an N-Acetylglucosamine Donor Armed by a 4-O-TBDMS Protecting Group
title_full_unstemmed A Direct Method for β-Selective Glycosylation with an N-Acetylglucosamine Donor Armed by a 4-O-TBDMS Protecting Group
title_short A Direct Method for β-Selective Glycosylation with an N-Acetylglucosamine Donor Armed by a 4-O-TBDMS Protecting Group
title_sort direct method for β-selective glycosylation with an n-acetylglucosamine donor armed by a 4-o-tbdms protecting group
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6155425/
https://www.ncbi.nlm.nih.gov/pubmed/28282905
http://dx.doi.org/10.3390/molecules22030429
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