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.
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.
authors.affiliation: Faculty of Pharmacy, Shaanxi University of Science & Technology, 6 Xuefu Road, Xi'an 710021, China. chengyuanliang@gmail.com.
authors.forename: Chengyuan
authors.initials: C
authors.lastname: Liang
authors.affiliation: Faculty of Pharmacy, Shaanxi University of Science & Technology, 6 Xuefu Road, Xi'an 710021, China. juweihui11521@sina.com.
authors.forename: Weihui
authors.initials: W
authors.lastname: Ju
authors.affiliation: Faculty of Pharmacy, Shaanxi University of Science & Technology, 6 Xuefu Road, Xi'an 710021, China. 18792439483@163.com.
authors.forename: Shunjun
authors.initials: S
authors.lastname: Ding
authors.affiliation: Faculty of Pharmacy, Shaanxi University of Science & Technology, 6 Xuefu Road, Xi'an 710021, China. hansun0618@163.com.
authors.forename: Han
authors.initials: H
authors.lastname: Sun
authors.affiliation: Faculty of Pharmacy, Shaanxi University of Science & Technology, 6 Xuefu Road, Xi'an 710021, China. maogennian@sust.edu.cn.
authors.forename: Gennian
authors.initials: G
authors.lastname: Mao
mesh_terms: D000964:Antimetabolites, Antineoplastic / Q000138:chemical synthesis*; D000069287:Capecitabine / Q000138:chemical synthesis*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D006031:Glycosylation; D009705:Nucleosides / Q000138:chemical synthesis*
chemical_list: D000964:Antimetabolites, Antineoplastic; D002712:Chlorides; D009705:Nucleosides; D000069287:Capecitabine
keywords: N-glycosylation; catalyst free reaction; glycosyl chiorides; nucleosides; silyl-Hilbert-Johnson reaction