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

Zhou, Longhu; Zhang, Hongwang; Li, Chengwei; De Schutter, Coralie; Sari, Ozkan; Mengshetti, Seema; Zhou, Shaoman; Kasthuri, Mahesh; Coats, Steven J; Schinazi, Raymond F; Amblard, Franck

Zhou, Longhu; Zhang, Hongwang; Li, Chengwei; De Schutter, Coralie; Sari, Ozkan; Mengshetti, Seema; Zhou, Shaoman; Kasthuri, Mahesh; Coats, Steven J; Schinazi, Raymond F; Amblard, Franck.

Afiliação

Zhou L; Center for AIDS Research, Laboratory of Biochemical Pharmacology, Department of Pediatrics, Emory University School of Medicine, and Children's Healthcare of Atlanta, 1760 Haygood Drive, Atlanta, Georgia 30322, United States.
Zhang H; Center for AIDS Research, Laboratory of Biochemical Pharmacology, Department of Pediatrics, Emory University School of Medicine, and Children's Healthcare of Atlanta, 1760 Haygood Drive, Atlanta, Georgia 30322, United States.
Li C; Center for AIDS Research, Laboratory of Biochemical Pharmacology, Department of Pediatrics, Emory University School of Medicine, and Children's Healthcare of Atlanta, 1760 Haygood Drive, Atlanta, Georgia 30322, United States.
De Schutter C; Center for AIDS Research, Laboratory of Biochemical Pharmacology, Department of Pediatrics, Emory University School of Medicine, and Children's Healthcare of Atlanta, 1760 Haygood Drive, Atlanta, Georgia 30322, United States.
Sari O; Center for AIDS Research, Laboratory of Biochemical Pharmacology, Department of Pediatrics, Emory University School of Medicine, and Children's Healthcare of Atlanta, 1760 Haygood Drive, Atlanta, Georgia 30322, United States.
Mengshetti S; Center for AIDS Research, Laboratory of Biochemical Pharmacology, Department of Pediatrics, Emory University School of Medicine, and Children's Healthcare of Atlanta, 1760 Haygood Drive, Atlanta, Georgia 30322, United States.
Zhou S; Center for AIDS Research, Laboratory of Biochemical Pharmacology, Department of Pediatrics, Emory University School of Medicine, and Children's Healthcare of Atlanta, 1760 Haygood Drive, Atlanta, Georgia 30322, United States.
Kasthuri M; Center for AIDS Research, Laboratory of Biochemical Pharmacology, Department of Pediatrics, Emory University School of Medicine, and Children's Healthcare of Atlanta, 1760 Haygood Drive, Atlanta, Georgia 30322, United States.
Coats SJ; Center for AIDS Research, Laboratory of Biochemical Pharmacology, Department of Pediatrics, Emory University School of Medicine, and Children's Healthcare of Atlanta, 1760 Haygood Drive, Atlanta, Georgia 30322, United States.
Schinazi RF; Center for AIDS Research, Laboratory of Biochemical Pharmacology, Department of Pediatrics, Emory University School of Medicine, and Children's Healthcare of Atlanta, 1760 Haygood Drive, Atlanta, Georgia 30322, United States.
Amblard F; Center for AIDS Research, Laboratory of Biochemical Pharmacology, Department of Pediatrics, Emory University School of Medicine, and Children's Healthcare of Atlanta, 1760 Haygood Drive, Atlanta, Georgia 30322, United States.

ACS Omega ; 7(1): 1452-1461, 2022 Jan 11.

Article em En | MEDLINE | ID: mdl-35036807

ABSTRACT

ABSTRACT

We present a newly developed synthetic route to 2-bromo-2-fluoro ribolactone based on our published 2-chloro-2-fluoro 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.

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Texto completo: 1 Coleções: 01-internacional Contexto em Saúde: 2_ODS3 Base de dados: MEDLINE Idioma: En Revista: ACS Omega Ano de publicação: 2022 Tipo de documento: Article

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