A new method for the synthesis of nucleoside 2′,3′- O, O-cyclic phosphorodithioates via aryl cyclic phosphites as intermediates

• Published in: Tetrahedron letters 2001-11, Vol.42 (45), p.8055-8058
• Main Authors: Wenska, Małgorzata, Jankowska, Jadwiga, Sobkowski, Michał, Stawiński, Jacek, Kraszewski, Adam
• Format: Article
• Language: English
• Subjects: cyclic phosphates; dithiophosphates; nucleosides; nucleotides
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/S0040-4039(01)01695-1

The reaction of 5′- O-protected ribonucleosides with tri(4-nitrophenyl) phosphite in the presence of pyridine furnished rapid formation of the corresponding 4-nitrophenyl 2′,3′- O, O-cyclic phosphites which upon sulfhydrolysis, followed by sulfurization of the resultant cyclic H-phosphonothioate and removal of the 5′- O-protecting groups, afforded nucleoside 2′,3′- O, O-cyclic phosphorodithioates in high yields. 5′-Protected ribonucleosides readily react with tris(4-nitrophenyl) phosphite to give the corresponding aryl nucleoside 2′,3′- O, O-cyclic phosphites. These upon sulfhydrolysis, followed by sulfurization and removal of the 5′-protecting groups afforded nucleoside 2′,3′- O, O-cyclophosphorodithioates in high yields.