Nucleosides and Nucleotides. XXXXV. Facile Deoxygenation of Neplanocin A and Nucleosides by the Use of Tri-n-butyltin Hydride

Abstract

2'(R)-Halogeno-2'-deoxyneplanocin A's were hydrogenated with tri-n-butyltin hydride to yield 2'-deoxyneplanocin A. The same compound was obtained by reduction of the 2'-O-(1-imidazolyl) thiocarbonyl derivative of neplanocin A. This procedure was also applicable to the synthesis of 2'-deoxyadenosine and-guanosine from the corresponding ribosides. Treatment of a neplanocin 2', 3'-O-cyclic thiocarbonate with tri-n-butyltin hydride gave 3'-deoxyneplanocin selectively in high yield.