EPIMERIZATION DURING THE ACETOLYSIS OF 3-O-ACETYL-5-O-BENZOYL-1,2-O-ISOPROPYLIDENE-3-C-METHYL-α-D-RIBOFURANOSE. SYNTHESIS OF 3'-C-METHYLNUCLEOSIDES WITH THE β-D-ribo- AND α-D-arabino CONFIGURATIONS

Article abstract of DOI:10.1016/0008-6215(88)84024-2

Acetolysis of 3-O-acetyl-5-O-benzoyl-1,2-O-isopropylidene-3-C-methyl-α-D-ribofuranose with a high concentration of acetic acid yielded 1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl-D-arabinofuranose, which was used for the preparation of 3-C-methyl-α-D-arabinofuranosyl nucleosides. 3'-C-Methylribonucleosides were also synthesized starting from 1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-C-methyl-D-ribofuranose.