3',5'-Bis-O-benzoyl-2'-deoxy-2'-fluoro-beta-D-arabinouridine

Base Information

• Chemical Name: 3',5'-Bis-O-benzoyl-2'-deoxy-2'-fluoro-beta-D-arabinouridine
• CAS No.: 128496-10-6
• Molecular Formula: C23H19FN2O7
• Molecular Weight: 454.411
• Mol file: 128496-10-6.mol

Synonyms:1-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-;

Chemical Property of 3',5'-Bis-O-benzoyl-2'-deoxy-2'-fluoro-beta-D-arabinouridine

Chemical Property:

• Melting Point: 185-187 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• PKA: 9.39±0.10(Predicted)
• PSA: 116.69000
• Density: 1.45±0.1 g/cm3(Predicted)
• LogP: 1.85470

Purity/Quality:

97% ^*data from raw suppliers

((2R,3R,4S,5R)-3-(Benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluorotetrahydrofuran-2-yl)methylbenzoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3',5'-Bis-O-benzoyl-2'-deoxy-2'-fluoro-beta-D-arabinouridine

There total 6 articles about 3',5'-Bis-O-benzoyl-2'-deoxy-2'-fluoro-beta-D-arabinouridine 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: 84.2%

2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide (97614-44-3) + uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) → 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)uracil (128496-10-6)

Guidance literature:

uracil; With ammonium sulfate; lithium hexamethyldisilazane; for 20h; Reflux;

2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide; In chloroform; for 24h; Reflux;

DOI:10.1016/j.ejmech.2011.06.020

Reference yield:

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)uracil (128496-10-6)

Guidance literature:

Multi-step reaction with 2 steps

1: HBr; HOAc

2: CCl₄ / Heating

With hydrogen bromide; acetic acid; In tetrachloromethane;

DOI:10.1081/NCN-200060300

Reference yield:

2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide (97614-44-3) + O,O'-bis-(trimethylsilyl)uracil (10457-14-4) → 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)uracil (128496-10-6)

Guidance literature:

In tetrachloromethane; for 60h; Heating;

DOI:10.1021/jo00236a017

upstream raw materials:

2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide

uracil

O,O'-bis-(trimethylsilyl)uracil

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

Downstream raw materials:

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

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

1-(2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl)cytosine

1-<2-deoxy-2-fluor-3-O-(methylsulfonyl)-5-O-trityl-β-D-arabinofuranosyl>)uracil

Refernces

• 1、 Wang, Qiang,Hu, Weidong,Wang, Shuyang,Pan, Zhenliang,Tao, Le,Guo, Xiaohe,Qian, Keduo,Chen, Chin-Ho,Lee, Kuo-Hsiung,Chang, Junbiao. "Synthesis of new 2′-deoxy-2′-fluoro-4′-azido nucleoside analogues as potent anti-HIV agents". experimental part. p. 4178 - 4183. Retrieved 2011/11/13.
• 2、 Moukha-Chafiq,Tiwari,Secrist III. "Synthesis of some 2′-fluoro-2′-deoxy-3′-C-ethynyl and 3′-C-vinyl-β-D-lyxofuranosyl nucleosides". . p. 713 - 715. Retrieved 2007/10/03.