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Molecules 2017, 22(1), 84; doi:10.3390/molecules22010084

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

Faculty of Pharmacy, Shaanxi University of Science & Technology, 6 Xuefu Road, Xi’an 710021, China
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Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 20 November 2016 / Revised: 10 December 2016 / Accepted: 15 December 2016 / Published: 5 January 2017
(This article belongs to the Section Bioorganic Chemistry)
View Full-Text   |   Download PDF [1157 KB, uploaded 5 January 2017]   |  

Abstract

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. View Full-Text
Keywords: nucleosides; glycosyl chiorides; N-glycosylation; catalyst free reaction; silyl-Hilbert-Johnson reaction nucleosides; glycosyl chiorides; N-glycosylation; catalyst free reaction; silyl-Hilbert-Johnson reaction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Liang, C.; Ju, W.; Ding, S.; Sun, H.; Mao, G. 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. Molecules 2017, 22, 84.

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