Synthesis of (5'S)-1;1',2',3',4',5'-13C5>-Thymidine via Stereoselective Deuteration of a 5-Oxoribose Derivative

Article abstract of DOI:10.1016/S0040-4039(96)02279-4

(5'S)-<5'-2H₁:1',2'3'4'5'-13C₅>-Thymidine has been synthesized by a stereoselective deuteride transfer reaction from (-)- or (+)-<2-2H₁>-isobornyloxymagnesium bromide to a 5-oxoribose derivative, which can be readily prepared from <13C₆>-D-glucose.The overall yield from D-glucose to thymidine was 27percent.The various nucleosides with a stereoselective 2H-label together with 13C at the C5' position, which have become available by the present method, will be quite useful for stereospecific assignment of the diastereotopic C5' methylene signals, and also for conformational analyses of the O5'-C5' bonds in nucleic acid oligomers.