SYNTHESE DE NUCLEOSIDES PYRIMIDIQUES A PARTIR DE 1,2-ANHYDRO-4-DESOXY-3-O-METHYL-PENTOPYRANOSES

Article abstract of DOI:10.1016/0008-6215(83)88186-5

Monotosylation of 4-deoxy-3-O-methyl-DL-threo- and erythro-pentopyranose led, in 62-68 percent yield, to the 2-O-tosyl derivatives which, on treatment at room temperature with sodium hydride in anhydrous ether, gave quantitatively 1,2-anhydro-4-deoxy-3-O-methyl-DL-threo- and erythro-pentopyranose, respectively.These epoxides reacted with 2,4-dimethoxypyrimidine in the presence of pyridinium hydrochloride to give, in 68-78 percent yield, 1-(4-deoxy-3-O-methyl-β-DL-erythro- and α,β-DL-threo-pentopyranosyl)-4-methoxy-2-pyrimidinone, respectively.Isomers having a trans-1',2' configuration were preponderantly formed by an SN2 reaction.