Methyl-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxylate

Base Information

• Chemical Name: Methyl-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxylate
• CAS No.: 38934-69-9
• Molecular Formula: C9H13N3O6
• Molecular Weight: 259.219
• Mol file: 38934-69-9.mol

Synonyms:1-b-D-Ribofuranosyl-1,2,4-triazole-3-carboxylicacid methyl ester;Methyl 1-(b-D-ribofuranosyl)-1,2,4-triazole-3-carboxylate;NSC 360639;

Chemical Property of Methyl-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxylate

Chemical Property:

• Vapor Pressure: 1.94E-13mmHg at 25°C
• Refractive Index: 1.701
• Boiling Point: 561.4 °C at 760 mmHg
• Flash Point: 293.3 °C
• PSA: 126.93000
• Density: 1.82g/cm³
• LogP: -2.32380
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98%min ^*data from raw suppliers

1-b-D-Ribofuranosyl-1,2,4-triazole-3-carboxylic acid methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Ribavirin impurity H. Ribavirin

Technology Process of Methyl-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxylate

There total 5 articles about Methyl-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

methyl 1H-1,2,4-triazole-3-carboxylate (4928-88-5) + 1,2,3,5-tetraacetylribose (13035-61-5) → methyl 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylate (38934-69-9)

Guidance literature:

With methanol; sodium iodide; at 65 ℃; for 1h; Reagent/catalyst;

Reference yield: 82.0%

1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester (57198-04-6,39925-10-5) → methyl 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylate (38934-69-9)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2007.03.018

Reference yield:

inosine (58-63-9) → methyl 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylate (38934-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aluminum (III) chloride / methanol / 2 h / 60 °C

2: methanol; sodium iodide / 1 h / 65 °C

With methanol; aluminum (III) chloride; sodium iodide; In methanol;

upstream raw materials:

1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester

inosine

methyl 1H-1,2,4-triazole-3-carboxylate

1,2,3,5-tetraacetylribose

Downstream raw materials:

methyl 1-(2,3-O-isopropylidene-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxylate

ribavirin

Refernces

• 1、 -. "Ribavirin compound containing one-twentieth water". Paragraph 0047; 0050; 0051. . Retrieved 2019/01/23.
• 2、 Kumarapperuma, Sidath C.,Sun, Yanjie,Jeselnik, Marjan,Chung, Kiwon,Parker, William B.,Jonsson, Colleen B.,Arterburn, Jeffrey B.. "Structural effects on the phosphorylation of 3-substituted 1-β-d-ribofuranosyl-1,2,4-triazoles by human adenosine kinase". . p. 3203 - 3207. Retrieved 2008/02/03.