The Journal of Organic Chemistry

… and efficient synthesis of nucleoside 5'-0-(1-thiotriphosphates), 5'-triphosphates and 2', 3'-cyclophosphorothioates using 2-chloro-4H-1, 3, 2-benzodioxaphosphorin-4- …

J Ludwig, F Eckstein

Index: Ludwig, Janos; Eckstein, Fritz Journal of Organic Chemistry, 1989 , vol. 54, # 3 p. 631 - 635

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Citation Number: 395

Abstract

2-Chloro-4H-1, 3, 2-benzodioxaphosphorin-4-one phosphitylates the 5'-hydroxy group of a nucleoside to form an intermediate (2), which on subsequent reaction with pyrophosphate produces, in a double displacement process, a Pz, F-dioxo-P1-5'- nucleosidylcyclotriphophite (3). Oxidation with sulfur gives a nucleoside 5'-(1- thiocyclotriphosphate)(4), which is hydrolyzed to the diastereomeric mixture of a ...