1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil

Base Information

• Chemical Name: 1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil
• CAS No.: 1333126-30-9
• Molecular Formula: C₂₃H₁₇ClFN₅O₇
• Molecular Weight: 529.869
• Mol file: 1333126-30-9.mol

Synonyms:1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil

Chemical Property of 1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 1-[4-Azido-3-O-benzoyl-5-O-(3-chlorobenzoyl)-(2-Deoxy-2-fluoro-b-D-arabinofuranosyl)uracil is reported to be a reactant used for the preparation of 2''-deoxy-2''-fluoro-4''-azido nucleoside analogs which exhibited extremely potent anti-HIV activity against NL4-3 (wild-type), NL4-3 (K101E), and RTMDR viral strains. Also it is used for the synthesis of 4-substituted fluoronucleoside analogs for the treatment of Hepatitis B virus infection.

Technology Process of 1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil

There total 10 articles about 1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil 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: 71.3%

1-(4-azido-2,5-dideoxy-2-fluoro-5-iodo-β-D-arabino-furanosyl)uracil (173379-67-4) + benzoyl chloride (98-88-4) + 3-chloro-benzenecarboperoxoic acid (937-14-4) → 1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil (1333126-30-9)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 8h;

Reference yield: 69.0%

1-(4'-azido-3'-O-benzoyl-2'-deoxy-2'-fluoro-5'-iodo-β-D-arabinofuranosyl)uracil (1145869-36-8) + 3-chlorobenzoate (535-80-8) → 1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil (1333126-30-9)

Guidance literature:

With dipotassium hydrogenphosphate; tetra(n-butyl)ammonium hydrogensulfate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; at 0 - 20 ℃;

Reference yield:

1-(2,5-dideoxy-2-fluoro-5-iodo-β-D-arabino-furanosyl)uracil (173379-62-9) → 1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil (1333126-30-9)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium methylate / methanol / 3 h / 65 °C

2: sodium azide; Iodine monochloride / tetrahydrofuran / 20 °C

3: dmap; triethylamine / dichloromethane

4: dipotassium hydrogenphosphate; tetra(n-butyl)ammonium hydrogensulfate; 3-chloro-benzenecarboperoxoic acid / dichloromethane; water / 20 °C

With dmap; dipotassium hydrogenphosphate; sodium azide; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; Iodine monochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/j.ejmech.2011.06.020

upstream raw materials:

1-(2,5-dideoxy-2-fluoro-5-iodo-β-D-arabino-furanosyl)uracil

4′,5′-didehydro-2′,5′-dideoxy-2′-fluoroarabinouridine

1-(4-azido-2,5-dideoxy-2-fluoro-5-iodo-β-D-arabino-furanosyl)uracil

1-(4'-azido-3'-O-benzoyl-2'-deoxy-2'-fluoro-5'-iodo-β-D-arabinofuranosyl)uracil

Downstream raw materials:

4′-azido-2′-deoxy-2′-fluoro-β-D-arabinocytidine

1-((2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydro-furan-2-yl)pyrimidine-2,4(1H,3H)-dione

Refernces

• 1、 -. "PYRIMIDINE NUCLEOSIDE DERIVATIVES, SYNTHESIS METHODS AND USES THEREOF FOR PREPARING ANTI-TUMOR AND ANTI-VIRUS MEDICAMENTS". Paragraph 0028. . Retrieved 2013/11/19.