Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction

An effective synthesis of nucleosides using glycosyl chlorides as glycosyl donors in the absence of Lewis acid has been developed. Glycosyl chlorides have been shown to be pivotal intermediates in the classical silyl-Hilbert-Johnson reaction. A possible mechanism that differs from the currently acce...

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Detalles Bibliográficos
Autores principales: Liang, Chengyuan, Ju, Weihui, Ding, Shunjun, Sun, Han, Mao, Gennian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6155650/
https://www.ncbi.nlm.nih.gov/pubmed/28067759
http://dx.doi.org/10.3390/molecules22010084
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author Liang, Chengyuan
Ju, Weihui
Ding, Shunjun
Sun, Han
Mao, Gennian
author_facet Liang, Chengyuan
Ju, Weihui
Ding, Shunjun
Sun, Han
Mao, Gennian
author_sort Liang, Chengyuan
collection PubMed
description An effective synthesis of nucleosides using glycosyl chlorides as glycosyl donors in the absence of Lewis acid has been developed. Glycosyl chlorides have been shown to be pivotal intermediates in the classical silyl-Hilbert-Johnson reaction. A possible mechanism that differs from the currently accepted mechanism advanced by Vorbrueggen has been proposed and verified by experiments. In practice, this catalyst-free method provides easy access to Capecitabine in high yield.
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spelling pubmed-61556502018-11-13 Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction Liang, Chengyuan Ju, Weihui Ding, Shunjun Sun, Han Mao, Gennian Molecules Communication An effective synthesis of nucleosides using glycosyl chlorides as glycosyl donors in the absence of Lewis acid has been developed. Glycosyl chlorides have been shown to be pivotal intermediates in the classical silyl-Hilbert-Johnson reaction. A possible mechanism that differs from the currently accepted mechanism advanced by Vorbrueggen has been proposed and verified by experiments. In practice, this catalyst-free method provides easy access to Capecitabine in high yield. MDPI 2017-01-05 /pmc/articles/PMC6155650/ /pubmed/28067759 http://dx.doi.org/10.3390/molecules22010084 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
Liang, Chengyuan
Ju, Weihui
Ding, Shunjun
Sun, Han
Mao, Gennian
Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction
title Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction
title_full Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction
title_fullStr Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction
title_full_unstemmed Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction
title_short Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction
title_sort effective synthesis of nucleosides utilizing o-acetyl-glycosyl chlorides as glycosyl donors in the absence of catalyst: mechanism revision and application to silyl-hilbert-johnson reaction
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6155650/
https://www.ncbi.nlm.nih.gov/pubmed/28067759
http://dx.doi.org/10.3390/molecules22010084
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