AN IMPROVED SYNTHETIC PREPARATION OF ANTI CONFORMATIONALLY CONSTRAINED ACYCLIC NUCLEOSIDES

Abstract

Practical large-scale synthesis of anti conformationally constrained acyclic nucleosides has been attained from the coupling of lithiated 2,4-dimethoxy-5,6-dimethylpyrimidine with 1,3-bis(tert-butyldiphenylsilyloxy)-propan-2-one, followed by the sequential reactions of methylthiomethylation, ring cyclization, hydrolysis, and desilylation.

ACKNOWLEDGMENTS

We thank Dr. Leroy B. Townsend for supplying 2,4-dimethoxy-5,6-dimethyl pyrimidine as a gift for starting material for chemical synthesis. This investigation is supported by a research grant from the National Science Council of the Republic of China (No. NSC 88-2314-B-016-046).