1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide

Base Information

• Chemical Name: 1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide
• CAS No.: 40372-06-3
• Molecular Formula: C₈H₁₂N₄O₄
• Molecular Weight: 228.208
• DSSTox Substance ID: DTXSID001153248
• Nikkaji Number: J1.576.078H
• Mol file: 40372-06-3.mol

Synonyms:40372-06-3;1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide;2/'-Deoxyribavirin;SCHEMBL11654052;DTXSID001153248;1-(2-Deoxy-beta-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide;1-(2-Deoxy-beta-D-erythro-pentofuranosyl)-1H-1,2,4-triazole-3-carboxamide

Chemical Property of 1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide

Chemical Property:

• XLogP3: -0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 228.08585488
• Heavy Atom Count: 16
• Complexity: 277

Purity/Quality:

97% ^*data from raw suppliers

2''-Deoxyribavirin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(OC1N2C=NC(=N2)C(=O)N)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=NC(=N2)C(=O)N)CO)O
• Uses: 2'-Deoxyribavirin, is an intermediate used for the synthesis of 2’-Deoxyribavirin-5’-triphosphate (D249940), which is a potential new inhibitor for HIV-1 replication. In addition, the triphosphate analog may be incorporated with several naturally occuring nucleosides. 2''-Deoxyribavirin, is an intermediate used for the synthesis of 2’-Deoxyribavirin-5’-triphosphate (D249940), which is a potential new inhibitor for HIV-1 replication. In addition, the triphosphate analog may be incorporated with several naturally occuring nucleosides.

Technology Process of 1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide

There total 6 articles about 1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide 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%

2'-deoxyuridine (951-78-0,63844-76-8) + 1,2,4-triazole-3-carboxamide (3641-08-5) → 1-(2'-deoxy-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide (40372-06-3)

Guidance literature:

With aeromonas hydrophila CECT 4226; at 45 ℃; for 1h; pH=7; aq. phosphate buffer; Enzymatic reaction;

DOI:10.3109/10242422.2010.538949

Reference yield: 74.0%

C20H38N4O5Si2 (359861-06-6) → 1-(2'-deoxy-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide (40372-06-3)

Guidance literature:

With triethylamine trihydrofluoride; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1080/15257770701490902

Reference yield:

1,2,4-triazole-3-carboxamide (3641-08-5) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 1-(2'-deoxy-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide (40372-06-3)

Guidance literature:

With Geobacillus kaustophilus ATCC 8005; In aq. phosphate buffer; at 60 ℃; pH=7; Green chemistry;

DOI:10.1016/j.molcatb.2015.08.006

upstream raw materials:

ribavirin

C₂₀H₃₈N₄O₅Si₂

2'-deoxyuridine

1,2,4-triazole-3-carboxamide

Downstream raw materials:

1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-1H-[1,2,4]triazole-3-carboxylic acid amide

2'-deoxyribavirin triphosphate

1-(2'-deoxy-β-D-erythro-pentofuranosyl)-(1H)-1,2,4-triazole-3-carboxamide-5'-tosylate

Refernces

• 1、 Nbile, Matas,Terreni, Marco,Lewkowicz, Elizabeth,Iribarren, Adolfo M.. "Aeromonas hydrophila strains as biocatalysts for transglycosylation". scheme or table. p. 395 - 402. Retrieved 2011/10/08.
• 2、 Pochet, Sylvie,Dugue, Laurence. "Imidazole-4-carboxamide and 1,2,4-triazole-3-carboxamide deoxynucleotides as simplified DNA building blocks with ambiguous pairing capacity". . p. 2003 - 2009. Retrieved 2007/10/03.