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

页码：1452 / 1461

页数：10

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