390
Tan et al.
Typical Procedure for the Preparation of 3. A mixture of 1,2,3,5-tetra-O-acetyl-β-D-
ribofuranose (47.1 g, 0.15 mol) and methyl 1,2,4-triazole-3-carboxylate (21.6 g, 0.17 mol)
and TfOH (0.11 g, 0.75 mmol) was heated with vigorous stirring at 135◦C for 2 h under
vacuum (about 55 mmHg). The solid obtained was then recrystallized from methanol,
collected and dried to give 53.1 g (92%) of 3 as a white solid, mp. 106–108◦C, lit.8 mp.
107–109◦.
Typical Procedure for the Preparation of Ribavirin (4). A mixture of 1,2,3,5-tetra-O-
acetyl-β-D-ribofuranose (47.1 g, 0.15 mol) and methyl 1,2,4-triazole-3-carboxylate (21.6 g,
0.17 mol), TfOH (0.11 g, 0.75 mmol) was heated under vigorous stirring at 135◦ for 2 h under
vacuum(about 55 mmHg). Methanol (100 mL) was added and NH3 gas was introduced
into the reaction mixture for 40 hrs at 20◦. The solvent was removed by distillation, and
the residual solid was recrystallized from EtOH and dried under vacuum at 60◦ for 10 h to
give 31.1 g (83%) of 4 as a white soild, mp. 169–170◦C, lit.8 mp. 166–168◦C. The overall
yield from the former procedure was 71% based on guanosine.
Acknowledgement
The authors wish to thank the financial help provided by Zhejiang Chengyi Pharmaceutical
Co., Ltd.
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