47281-07-2Relevant academic research and scientific papers
SYNTHESIS OF 2'(3')-PHOSPHATES AND 2'(3')-PHOSPHOROTHIOATES OF 5'-O-CARBOXYMETHYLINOSINE AND RELATED COMPOUNDS
Holy, Antonin,Kois, Pavol
, p. 2817 - 2829 (2007/10/02)
5'-O-Carboxymethylinosine (IX) was prepared from disodium salt of 2',3'-O-isopropylideneinosine (VIII) by treatment with sodium chloroacetate, followed by acid hydrolysis. 5'-O-(2-Aminoethylamidocarbonylmethyl)inosine (XIII) was obtained by reaction of IX with p-nitrophenol and subsequent treatment with ethylenediamine.Action of triethyl phosphite on the compounds IX and XIII afforded the corresponding 5'-O-substituted 2'(3')-phosphites X and XIV which on reaction with trimethylsilyl chloride and sulfur gave the 2'(3')-phosphorothioates XI and XV.The compound IX was transformed by phosphorus oxychloride in 5'-O-carboxymethylinosine 2'(3')-phosphate (XII).Uridine, adenosine and inosine 2'(3')-phosphorothioates (Ia-Ic) were obtained from 2',3'-O-di-n-butylstannylene derivatives of the nucleosides IV by treatment with thiophosphoryl chloride followed by alkaline hydrolysis; inosine and guanosine 2'(3')-phosphorothioates (Ic, Id) were prepared by reaction of the corresponding 2'(3')-phosphites VIc, VId with trimethylsilyl chloride and sulfur.Cyclisation of Ic and Id with ethyl chloroformate in the presence of tri-n-butylamine afforded inosine 2',3'-O,O-cyclophosphorothioate (VIIc) and the corresponding guanosine derivative VIId.Compounds VIIc and VIId are not cleaved by Streptomyces aureofaciens ribonuclease.
