NUCLEIC ACID RELATED COMPOUNDS. 42. A GENERAL PROCEDURE FOR THE EFFICIENT DEOXYGENATION OF SECONDARY ALCOHOLS. REGIOSPECIFIC AND STEREOSELECTIVE CONVERSION OF RIBONUCLEOSIDES TO 2 prime -DEOXYNUCLEOSIDES.

Article abstract of DOI:10.1021/ja00350a052

Treatment of unhindered secondary alcohols with phenoxythiocarbonyl chloride (phenyl chlorothionocarbonate) in pyridine/dichloromethane, or in acetonitrile with 4-dimethylaminopyridine catalysis for hindered alcohols, gave clean conversion to their O-phenoxythiocarbonyl derivatives. Reductive deoxygenation of these phenyl thionocarbonate esters proceeded smoothly, using tri-n-butyltin hydride and a free radical initiator in warm toluene. Overall conversion yields ranged from 57 to 78% for the naturally occurring nucleosides, nucleoside antibiotics, and methyl beta -D-ribofuranoside.