1,2,3,5-Tetraacetyl-beta-D-ribofuranose → Methyl 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylate

Participants

Reaction Steps

A mixture of methyl 1,2,4-triazole-3-carboxylate (12.7 g., 0.10 mol) and 1,2,3,5-tetra-O-acetyl-β -D-ribofuranose (31.8 g., 0.10 mol) was heated in an oil bath maintained at 160-165° until the sugar had melted. Bis(p-nitrophenyl) phosphate (250 mg.) was added and heating at 160-165° was continued with stirring under diminished pressure for 15-20 min. The residue was dissolved in hot benzene, the solution was filtered and cyclohexane was added to the filtrate to give the crystalline product (30.0 g., 77.8%) with M.P. 107-109°.

Provenance & Evidence