SYNTHESIS OF D-RIBO-C-NUCLEOSIDE ANALOGUES BY DEHYDRATION OF NEW D-ALLO-PENTITOL-1-YL HETEROCYCLES

Article abstract of DOI:10.1016/S0008-6215(00)90702-X

The reaction of 2-amino-2-deoxy-D-glycero-D-altro-heptose hydrochloride with acyclic and cyclic 1,3-dicarbonyl compounds gives, respectively, (D-allo-pentitol-1-yl)-pyrroles and -tetrahydroindoles that can be dehydrated to yield D-ribo-C-glycosyl heterocycles having furanoid or pyranoid structures, depending on the reaction conditions.Thus, when the reactions were kinetically controlled, α- and β-D-ribofuranosyl heterocycles were obtained, but α- and β-D-ribopyranosyl heterocycles were formed under conditions of thermodynamic control.A criterion is proposed to differentiate between both structures on the basis of the mass spectra of their triacetates.