Several p-D-ribonucleosides were synthesized in high yields under mild conditions by N-glycosylations of methyl 2,3,5-tri-O-benzoyl-~-D-ribofuranosylcarbonate (1) with trimethylsilylated nucleoside bases in acetonitrile using a catalytic amount of metal iodide such as SnI2, SbI3 or Te14. A deprotection of N6-benzoyl group of coupling product took place to a considerable extent when N6-benzoyl-N6@-bis(trimethylsily1)adenine was employed as a nucleoside base using Sn12 or SnClz as a catalyst while it was minimized when SbI3 or TeI4 was used. Further, the Nglycosylation of 1 with 7-trimethylsilyltheophylline in the presence of a catalytic amount of metal iodide was more effectively achieved in nitrile solvents other than acetonitrile.The chemistry and biochemistry of nucleic acids are getting more and more important because nucleic acids play significant roles on the determination of nature and function of organisms, on the reproduction for conservation of species and on the control of biological processes such as metabolisms and biosyntheses. Nucleosides which are the components of nucleic acids also have many essential functions such as regulating enzyme and cell activities and having physiological control of blood pressure.l Therefore, analogs of nucleosides are used as therapeutic agents such as antitumor (araC) and antiviral agents (e.g., ACV, araA, AZT and ddI), and even more # This paper is dedicated to Dr. Yoshihisa Mizuno on the occasion of his 75th birthday. 17

β-d-Ribonucleosides are stereoselectively synthesized in high yields from methyl 2,3,5-tri-O-benzoyl-β-d-ribofuranosyl carbonate and trimethylsilylated nucleoside bases by the use of [diphenyltin sulfide/silver salt] or [Lawesson’s reagent/silver salt] combined catalyst system under mild conditions.

Catalytic stereoselective synthesis of several ribonucleosides from 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl methyl carbonate and trimethylsilylated nucleoside bases is efficiently carried out by combined use of silver salts and diphenyltin sulfide (Ph2Sn=S) under mild conditions.

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