Highly efficient synthesis of 2′, 3′-didehydro-2′, 3′-dideoxy-β-nucleosides through a sulfur-mediated reductive 2′, 3′-trans-elimination. From …

LÁ de Cienfuegos, AJ Mota, C Rodríguez, R Robles

Index: Robles, Rafael; Rodriguez, Concepcion; Alvarez De Cienfuegos, Luis; Mota, Antonio J. Tetrahedron Asymmetry, 2004 , vol. 15, # 5 p. 831 - 838

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Citation Number: 6

Abstract

Taking into account the thiophilic properties of iodine, a very simple methodology to achieve 2′, 3′-didehydro-2′, 3′-dideoxy-β-nucleosides in high yield was performed, using mild, and inexpensive conditions, by means of the treatment of 2′-deoxy-3′, 5′-dibenzoyl-2′- iodo-β-nucleoside derivatives with NaHS. The process has shown to be highly dependent of the relative geometry between the iodine atom and the adjacent leaving group. In this way ...