Diastereoselective Synthesis of 2′-Dihalopyrimidine Ribonucleoside Inhibitors of Hepatitis C Virus Replication

被引：1
|
作者：
Zhou, Longhu [1 ,2 ]
Zhang, Hongwang [1 ,2 ]
Li, Chengwei [1 ,2 ]
De Schutter, Coralie [1 ,2 ]
Sari, Ozkan [1 ,2 ]
Mengshetti, Seema [1 ,2 ]
Zhou, Shaoman [1 ,2 ]
Kasthuri, Mahesh [1 ,2 ]
Coats, Steven J. [1 ,2 ]
Schinazi, Raymond F. [1 ,2 ]
Amblard, Franck [1 ,2 ]
机构：
[1] Emory Univ, Ctr AIDS Res, Dept Pediat, Lab Biochem Pharmacol,Sch Med, Atlanta, GA 30322 USA
[2] Childrens Healthcare Atlanta, Atlanta, GA 30322 USA
来源：
ACS OMEGA | 2022年 / 7卷 / 01期
关键词：
SODIUM-SALT GLYCOSYLATION; ANTIVIRAL THERAPY; NS5B POLYMERASE; NUCLEOSIDE; HCV; NUCLEOTIDE; POTENT; PRODRUGS;
D O I：
10.1021/acsomega.1c06174
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We present a newly developed synthetic route to 2-bromo-2-fluoro ribolactone based on our published 2-chloro-2fluoro ribolactone synthesis. Stereoselective fluorination is key to controlling the 2-diastereoselectivity. We also report a substantially improved glycosylation reaction with both the 2-bromo-2-fluoro and 2-chloro-2-fluoro sugars. These improvements allowed us to prepare 2'-dihalo nucleosides 13 and 14 in an overall 15-20% yield.
引用
收藏
页码：1452 / 1461
页数：10
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