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Paper | Special issue | Vol 47, No. 1, 1998, pp.349-356
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)27
Efficient Synthesis of Specifically Deuterated Nucleosides: Preparation of 4'-Deuteriothymidine

Michael E. Jung* and Yue Xu

*Department of Chemistry and Biochemistry, University of California, 405 Hilgard Avenue Los Angels, CA 90095-1569, U.S.A.

Abstract

A very straightforward synthesis of 4’-deuteriothymidine (1) from inexpensive thymidine (2) is described. The key step involves triple deprotonation of the ester prepared by selective oxidation of unprotected thymidine (and esterification) and deuteration from the α-face to produce the desired 4’-deuterio derivative (5) which is then taken on to 1. Thus one can prepare the 4’-deuteriothymidine (1) in only five steps from thymidine (2) in an overall yield of 16%.