Application of the wittig and kolbe reactions to uridine derivatives: attempted synthesis of the nucleotide analogue, 5′-Carboxymethyl-5′-deoxyuridine

Abstract

The Wittig reaction between (ethoxycarbonylmethylene)triphenylphosphorane and 1-(2,3- O-isopropylidene-β- d- ribopentodialdo-1,4-furanosyl)uracil gave 1-(5,6-dideoxy-2,3- O-isopropylidene-β- d- erythro-hept-4-enofuranosyluronic acid)uracil and 1-(3,5,6-trideoxy-β- d- glycero-hept-3,5-dienofuranosyluronic acid)uracil. An anodic (Kolbe) coupling reaction between methyl hydrogen succinate and 1-(β- d-ribofuranosyluronic acid)uracil gave, in low yield, a mixture of 5′-carboxymethyl-5′-deoxyuridine [1-(5,6-dideoxy-β- d- ribo-heptofuranosyluronic acid)uracil] with its α- l- lyxo isomer, as their methyl esters. 5-Methoxycarbonylethyluracil was also formed.