EFFICIENT SYNTHESIS OF SPECIFICALLY DEUTERATED NUCLEOSIDES - PREPARATION OF 4'-DEUTERIOTHYMIDINE

A very straightforward synthesis of 4'-deuteriothymidine (1) from inex pensive thymidine (2) is described. The key step involves triple depro tonation of the ester prepared by selective oxidation of unprotected t hymidine (and esterification) and deuteration from the alpha-face to p roduce the desired 4'-deuterio derivative (5) which is then taken on t o 1. Thus one can prepare the 4'-deuteriothymidine (1) in only five st eps from thymidine (2) in an overall yield of 16%.