Synthesis of Methyl 1-(2,3,5-Tri-O-acetyl--L-ribofuranosyl)-1,2,4- triazole-3-carboxyla
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- 作者：Pingsheng Zhang ; Zhiming E. Dong ; and Thomas P. Cleary
- 刊名：Organic Process Research & Development
- 出版年：2005
- 出版时间：September 2005
- 年：2005
- 卷：9
- 期：5
- 页码：583 - 592
- 全文大小：192K
- 年卷期：v.9,no.5(September 2005)
- ISSN：1520-586X
文摘
A two-step manufacturing process for methyl 1-(2,3,5-tri-O-acetyl-
-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate (1) wasdeveloped. In step 1, L-ribose was converted to a /
mixtureof 1,2,3,5-tetra-O-acetyl-L-ribofuranoses (2 and 4). The stepcontained four chemical transformations and was completedin "one-pot" in approximately 95% yield. The crude step 1product was reacted with methyl 1,2,4-triazole-3-carboxylate(3) in step 2 to produce 1. The successful utilization of bothisomers (2 and 4) in step 2 offered advantages of higher overallyield and a much simplified process by eliminating the isolationof pure 2. The process was successfully scaled up to the pilotplant and subsequently in a manufacturing campaign usingcommercial production facilities.
-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate (1) wasdeveloped. In step 1, L-ribose was converted to a / mixtureof 1,2,3,5-tetra-O-acetyl-L-ribofuranoses (2 and 4). The stepcontained four chemical transformations and was completedin "one-pot" in approximately 95% yield. The crude step 1product was reacted with methyl 1,2,4-triazole-3-carboxylate(3) in step 2 to produce 1. The successful utilization of bothisomers (2 and 4) in step 2 offered advantages of higher overallyield and a much simplified process by eliminating the isolationof pure 2. The process was successfully scaled up to the pilotplant and subsequently in a manufacturing campaign usingcommercial production facilities.