Synthesis of Methyl 1-(2, 3, 5-Tri-O-acetyl-β-l-ribofuranosyl)-1, 2, 4-triazole-3-carboxylate from l-Ribose: From a Laboratory Procedure to a Manufacturing Process

P Zhang, ZE Dong, TP Cleary

Index: Zhang, Pingsheng; Dong, Zhiming E.; Cleary, Thomas P. Organic Process Research and Development, 2005 ,  vol. 9,  # 5  p. 583 - 592

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Citation Number: 8

Abstract

A two-step manufacturing process for methyl 1-(2, 3, 5-tri-O-acetyl-β-l-ribofuranosyl)-1, 2, 4- triazole-3-carboxylate (1) was developed. In step 1, l-ribose was converted to a β/α mixture of 1, 2, 3, 5-tetra-O-acetyl-l-ribofuranoses (2 and 4). The step contained four chemical transformations and was completed in “one-pot” in approximately 95% yield. The crude step 1 product was reacted with methyl 1, 2, 4-triazole-3-carboxylate (3) in step 2 to produce 1. ...