Efficient and Stereoselective Synthesis of 3′-Deoxy 3′ - C -Branched-Chain Substituted Thymidine - Archive ouverte HAL
Article Dans Une Revue Synthesis: Journal of Synthetic Organic Chemistry Année : 1994

Efficient and Stereoselective Synthesis of 3′-Deoxy 3′ - C -Branched-Chain Substituted Thymidine

Francoise Debart
Alain de Mesmaeker
  • Fonction : Auteur

Résumé

In this report, we provide for the first time a facile, efficient, and stereoselective synthesis of 1-[5-O-(tert-butyldiphenylsilyl)-2, 3-dideoxy-3-C-formyl-β-D-erythro-pentofuranosyl] thymine (12), using an intermolecular radical C-C bond formation reaction. The utility of this compound for antisense application is discussed and, as an extension, 12 was converted into 1-[2,3-dideoxy-3 -C-(hydroxymethyl)-β-D-erythro-pentofuranosyl]thymine (14), a potent antiviral and antitumor agent

Domaines

Chimie
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Dates et versions

hal-04650441 , version 1 (16-07-2024)

Identifiants

Citer

Yogesh Sanghvi, Ramesh Bharadwaj, Francoise Debart, Alain de Mesmaeker. Efficient and Stereoselective Synthesis of 3′-Deoxy 3′ - C -Branched-Chain Substituted Thymidine. Synthesis: Journal of Synthetic Organic Chemistry, 1994, 1994 (11), pp.1163-1166. ⟨10.1055/s-1994-25664⟩. ⟨hal-04650441⟩
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