Home
Resources
Publications
3'-Carbon-substituted Pyrimidine Nucleosides Having a 2',3'-dideoxy and 2',3'-didehydro-2',3'-dideoxy Structure: Synthesis and Antiviral Evaluation

3'-Carbon-substituted Pyrimidine Nucleosides Having a 2',3'-dideoxy and 2',3'-didehydro-2',3'-dideoxy Structure: Synthesis and Antiviral Evaluation

Hiroki Kumamoto, Sayoko Onuma, Hiromichi Tanaka, Ginger E Dutschman, Yung-Chi Cheng

Antivir Chem Chemother. 2006;17(4):225-34.

PMID: 17066900

Abstract:

The bis(tributylstannyl) derivative of 2',3'-didehydro-2',3'-dideoxyuridine (d4U) underwent an anionic 5'-O-->3'-C stannyl migration to yield the 3'-tributylstannyl-d4U. This compound, with its vinylstannane structure, allowed ready access to the preparation of 3'-carbon-substituted analogues through the Stille reaction. A conventional transformation of the uracil moiety of these d4U analogues led to the corresponding 2',3'-didehydro-2',3'-dideoxycytidine (d4C) counterparts. Some 2',3'-dideoxycytidine (ddC) analogues were also synthesized. Antiviral evaluation revealed that none of these analogues showed activity against HIV, hepatitis B virus, herpes simplex virus-1 (HSV-1) and HSV-2.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP153435633	2-(Tributylstannyl)pyrimidine		153435-63-3	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: