Synthesis of carbocyclic analogues of 4'-ethynyl- and 4'-cyano-d4T

Hiroki Kumamoto; Keisuke Kato; Kazuhiro Haraguchi; Hiromichi Tanaka; Takao Nitanda; Masanori Baba; Ginger E Dutschman; Yung-Chi Cheng

doi:10.1093/nass/48.1.41

Synthesis of carbocyclic analogues of 4'-ethynyl- and 4'-cyano-d4T

Nucleic Acids Symp Ser (Oxf). 2004:(48):41-2. doi: 10.1093/nass/48.1.41.

Authors

Hiroki Kumamoto¹, Keisuke Kato, Kazuhiro Haraguchi, Hiromichi Tanaka, Takao Nitanda, Masanori Baba, Ginger E Dutschman, Yung-Chi Cheng

Affiliation

¹ School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan.

PMID: 17150468
DOI: 10.1093/nass/48.1.41

Abstract

Synthesis of carbocyclic analogues of 4'-ethynyl and cyano-d4T (4 and 5) was investigated. The ethynyl or cyano group was constructed by conversion of the ester function of key intermediate 13. The carbocyclic unit 12 was prepared from readily available beta-keto ester 6.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acids, Carbocyclic / chemistry*
Anti-HIV Agents / chemical synthesis*
Anti-HIV Agents / chemistry
Stavudine / analogs & derivatives*
Stavudine / chemical synthesis
Stavudine / chemistry

Substances

4'-cyano-2',3'-didehydro-2',3'-dideoxythymidine
4'-ethynylstavudine
Acids, Carbocyclic
Anti-HIV Agents
Stavudine