2'-DEOXY-2'-FLUOROTHYMIDINE

Base Information

• Chemical Name: 2'-DEOXY-2'-FLUOROTHYMIDINE
• CAS No.: 122799-38-6
• Molecular Formula: C10H13FN2O5
• Molecular Weight: 260.222
• Hs Code.: 29389090
• Mol file: 122799-38-6.mol

Synonyms:2'-Deoxy-2'-fluorothymidine;2'-fluorothymidine;thymidine, 2'-fluoro-;

Chemical Property of 2'-DEOXY-2'-FLUOROTHYMIDINE

Chemical Property:

• Melting Point: 185-186 °C
• PKA: 9.55±0.10(Predicted)
• PSA: 104.55000
• Density: 1.55 g/cm³
• LogP: -1.56630

Purity/Quality:

99% ^*data from raw suppliers

1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione 95%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2'-DEOXY-2'-FLUOROTHYMIDINE

There total 6 articles about 2'-DEOXY-2'-FLUOROTHYMIDINE 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: 31.0%

O-2,2'-cyclo-5-methyluridine (22423-26-3) → 1-(2'-deoxy-2'-fluoro-β-D-ribofuranosyl)-5-methyluracil (122799-38-6,163252-36-6,2923-73-1)

Guidance literature:

With pyridine hydrogenfluoride; In 1,4-dioxane; at 120 - 125 ℃; for 18h;

DOI:10.1016/j.bmc.2004.12.011

Reference yield:

1-[(2R,3R,4R,5R)-3-Fluoro-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (910027-33-7) → 1-(2'-deoxy-2'-fluoro-β-D-ribofuranosyl)-5-methyluracil (122799-38-6,163252-36-6,2923-73-1)

Guidance literature:

With toluene-4-sulfonic acid; In methanol;

DOI:10.1016/S0960-894X(02)00551-6

Reference yield:

5-Methyluridine (1463-10-1,642082-80-2) → 1-(2'-deoxy-2'-fluoro-β-D-ribofuranosyl)-5-methyluracil (122799-38-6,163252-36-6,2923-73-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / diphenyl carbonate; NaHCO₃ / hexamethylphosphoric acid triamide / 0.5 h / 150 °C

2: 31 percent / HF*pyridine / dioxane / 18 h / 120 - 125 °C

With bis(phenyl) carbonate; sodium hydrogencarbonate; pyridine hydrogenfluoride; In 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/j.bmc.2004.12.011

upstream raw materials:

1-[(2R,3R,4R,5R)-3-Fluoro-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

O-2,2'-cyclo-5-methyluridine

1-(3,5-O-di(tetrahydropyran-2-yl)-β-D-arabinofuranosyl)thymine

5-Methyluridine

Downstream raw materials:

1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-4-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

C₁₀H₁₁FN₂O₆

1-(2-deoxy-2-fluoro-5-O-trityl-β-D-ribofuranosyl)-5-methyluracil

5'-O-(tert-butyldiphenylsilyl)-2',3'-dideoxy-2'-β-fluoro-3'-C-(2-phenylethenyl)-5-methyluridine

Refernces

• 1、 Shi, Junxing,Du, Jinfa,Ma, Tianwei,Pankiewicz, Krzysztof W.,Patterson, Steven E.,Hassan, Abdalla E. A.,Tharnish, Phillip M.,McBrayer, Tamara R.,Lostia, Stefania,Stuyver, Lieven J.,Watanabe, Kyoichi A.,Chu, Chung K.,Schinazi, Raymond F.,Otto, Michael J.. "Synthesis and in vitro anti-HCV activity of β-D- and L-2′-deoxy-2′-fluororibonucleosides". . p. 875 - 879. Retrieved 2007/10/03.
• 2、 Vanheusden, Veerle,Munier-Lehmann, Helene,Pochet, Sylvie,Herdewijn, Piet,Van Calenbergh, Serge. "Synthesis and evaluation of thymidine-5′-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase". . p. 2695 - 2698. Retrieved 2007/10/03.