A simple and efficient synthesis of puromycin, 2,2'-anhydro-pyrimidine nucleosides, cytidines and 2',3'-anhydroadenosine from 3',5'-O-sulfinyl xylo-nucleosides.

Synthesis of antibiotics, puromycin and 3'-amino-3'-deoxy-N6,N6-dimethyladenosine 11 was achieved by utilizing the cyclic sulfite 6a of the xylo-3',5'-dihydroxy group as a new protective group. The key synthetic step is the deprotection of the sulfite moiety through the intramolecular cyclization of 2-alpha-carbamate 7. In a similar manner 2,2'-anhydro-pyrimidine nucleosides 15, ribo-cytidines 17 and 2',3'-anhydroadenosine 14 were prepared in high yields from the corresponding sulfites 4, 5, and 6b, respectively.

Discovery of a novel route to 2'-deoxy and 2'-functional pyrimidine nucleosides via 3',5'-O-sulfinyl xylo-nucleosides.

We synthesized 2,2'-anhydro-pyrimidine nucleosides through a novel and efficient rearrangement with 3',5'-O-sulfinyl xylo nucleosides which were prepared from an inexpensive starting material, D-xylose. A variety of 2'-deoxy and 2'-functional pyrimidine nucleosides can be prepared from 2,2'-anhydro-pyrimidine nucleosides.