Direct and efficient synthesis of nucleosides through the ortho-(tert-butylethynyl)phenyl thioglycosides (BEPTs) protocol

Hui Liu, Ming-Yang Wang, Hua Xie, Yanli Qiu, Tian Mao, Xiaomei Shen, Xu-Xue Liu, Jing-Jing Guo, Ming-Ze Tang, Jin-Xi Liao, Yuan-Hong Tu, Liu De-Yong and Jian-Song Sun ()
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Hui Liu: Jiangxi Normal University
Ming-Yang Wang: Jiangxi Normal University
Hua Xie: Jiangxi Normal University
Yanli Qiu: Shanghai University of Traditional Chinese Medicine
Tian Mao: Jiangxi Normal University
Xiaomei Shen: Jiangxi Normal University
Xu-Xue Liu: Jiangxi Normal University
Jing-Jing Guo: Jiangxi Normal University
Ming-Ze Tang: Jiangxi Normal University
Jin-Xi Liao: Jiangxi Normal University
Yuan-Hong Tu: Jiangxi Normal University
Liu De-Yong: Jiangxi Normal University
Jian-Song Sun: Jiangnan University

Nature Communications, 2025, vol. 16, issue 1, 1-14

Abstract: Abstract Nucleosides are highly biologically relevant compounds, and are widely clinically used as drugs for the treatment of virus/bacteria infections and cancers. However, efficient chemical synthesis of nucleoside is highly difficult due to the low reactivity of nucleobases acceptors, challenging the existing synthetic protocols. Here we show an alternative synthetic protocol with judiciously designed o-(tert-butylethynyl)phenyl thioglycosides (BEPTs) as donors. The protocol is featured by stable glycosylation donors and high efficiency, direct glycosylation without the need for preactivation/silylation of nucleobases, broad substrate scope, capacity in furnishing 2-deoxy-nucleosides, cost efficiency, scalability, and significantly improved reaction speed, and exhibits favorable and profound solvent effects for hexafluoroisopropanol (HFIP). To check the practicality of the protocol, efficient preparation of angustmycin A and dJ is accomplished. The reaction mechanisms are systematically investigated, providing deep insights to the BEPT protocol.

Date: 2025
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DOI: 10.1038/s41467-025-63874-5

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