2,3,5-Tri-O-benzoyl-2-C-methyl-betaD-ribofuranose → 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose

Participants

Reaction Steps

One preferred embodiment of the present invention is exemplified in FIG. 1 and comprises reacting D-fructose in the presence of CaO/water at 23-40° C. for 6-22 hours, and then adding CO2 and oxalic acid to the reaction mixture and allowing the reaction to proceed for 8-12 hours to form 2-C-methyl-D-ribonic-γ-lactone (1); reacting 2-C-methyl-D-ribonic-γ-lactone (1) with 4-dimethylaminopyridine (DMAP) and triethylamine (TEA) in 1,2-dimethoxyethane (DME) at temperature of from about 5° C. to 25° C. for about 30 minutes, and then cooling the mixture to about 5° C. and adding benzoyl chloride to provide 2,3,5-tri-O-benzoyl-2-C-methyl-D-ribonic-γ-lactone (2); reacting 2,3,5-tri-O-benzoyl-2-C-methyl-D-ribonic-γ-lactone (2) with Red-Al/ethanol in toluene at a temperature of from about −5 to 0° C. for about 40 minutes to provide 2,3,5-tri-O-benzoyl-2-C-methyl-β-D-ribofuranose (3); and finally adding benzoyl chloride/TEA to a cold solution of 2,3,5-tri-O-benzoyl-2-C-methyl-β-D-ribofuranose (3) in the presence of DMAP and DME and allowing the reaction to proceed for from about 4 hours to about 12 hours at a temperature of from about 5 to about 50° C., thereby providing the final product (4), 2,3,5-tri-O-benzoyl-2-C-methyl-β-D-ribofuranose.

Provenance & Evidence