EFFICIENT SYNTHESIS OF D-[5-C-13]RIBOSE FROM D-RIBOSE AND ITS CONVERSION INTO [5'-C-13]NUCLEOSIDES

An approach to the synthesis of [5-C-13]ribose (6) was achieved by a s equence reaction as follows: periodate oxidation of 2,3-di-O-benzyl-D- ribose dibenzyl acetal (2), which was derived from D-ribose (1) in 70% overall yield in 8 steps, followed by the introduction of C-13 into t he 5-position of D-ribose by Wittig reaction using Ph(3)P(13)CH(3)I-Bu Li, highly diastereoselective hydroxylation with OsO4, and then debenz ylation. Compound 6 with the necessary protecting groups and a leaving group was derived into [5'-C-13]ribonucleoside derivatives by the cou pling reaction with persilylated nucleobases. Copyright (C) 1996 Elsev ier Science Ltd