FACILE STEREOSPECIFIC SYNTHESIS OF α-ANOMERIC 2'-DEOXYNUCLEOSIDES

Article abstract of DOI:10.3987/COM-92-6125

The coupling reaction of activated nucleobases, such as the sodium salts of N-benzoyladenine and 6-chloropurine and 2,4-bis-O-trimethylsilylthymine, with 1-α-chloro-2-deoxy-3,5-di-O-p-toluoylribofuranose (1) in a mixture of acetonitrile and tetrahydrofuran leads to the stereospecific formation of α-anomeric 2'-deoxynucleosides with satisfactory yields.The ratio of the distribution between the resulted α- and β-stereoisomers was about 3:1 in each case.The method is simple and applicable to the preparation of both purine and pyrimidine α-2'-deoxynucleosides.