2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose

Base Information

• Chemical Name: 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose
• CAS No.: 97614-43-2
• Molecular Formula: C26H21FO7
• Molecular Weight: 464.447
• Hs Code.: 29329990
• Mol file: 97614-43-2.mol

Synonyms:a-D-Arabinofuranose,2-deoxy-2-fluoro-, tribenzoate (9CI);2'-Fluoro-2'-deoxy-1,3,5-tri-O-benzoyl-a-D-arabinofuranose;1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinose;

Chemical Property of 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 74-77°C
• Refractive Index: 1.607
• Boiling Point: 584.1 °C at 760 mmHg
• Flash Point: 295.7 °C
• PSA: 88.13000
• Density: 1.35 g/cm³
• LogP: 3.98900
• Storage Temp.: 2-8°C
• Solubility.: Soluble in chloroform or dichloromethane

Purity/Quality:

98%, ^*data from raw suppliers

2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-α-D-arabinofuranose| ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: It is a pharmaceutical intermediate and is used as an OLED materials. Clofarabine intermediate.

Technology Process of 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose

There total 9 articles about 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose 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: 96.0%

→ 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) + 1,3,5-tri-O-benzoyl-α-D-ribofuranoside (22224-41-5)

Guidance literature:

Reference yield: 85.0%

2-O-<(trifluoromethyl)sulfonyl>-1,3,5-tri-O-benzoyl-α-D-ribofuranose (97614-41-0) → 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In ethyl acetate; at 80 ℃; for 24h;

DOI:10.1016/S0040-4020(98)00460-8

Reference yield: 83.0%

1,3,5-tri-O-benzoyl-α-D-ribofuranoside (22224-41-5) → 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2)

Guidance literature:

With (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane; at 50 ℃;

DOI:10.1081/NCN-120022961

upstream raw materials:

ethylene glycol

2-O-(imidazolylsulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose

2-O-(fluorosulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose

1,3,5-tri-O-benzoyl-α-D-ribofuranoside

Downstream raw materials:

((2R,3R,4S)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate

4-chloro-5-iodo-7-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

C₁₇H₁₇FN₄O₃

2-amino-6-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)-9H-purine

Refernces

• 1、 Dai, Qing,Lu, Xingyu,Zhang, Liang,He, Chuan. "Synthesis of DNA oligos containing 2′-deoxy-2′-fluoro-d- arabinofuranosyl-5-carboxylcytosine as hTDG inhibitor". scheme or table. p. 5145 - 5151. Retrieved 2012/08/13.
• 2、 Pillarsetty, Nagavarakishore,Cai, Shangde,Ageyeva, Lyudmila,Finn, Ronald D.,Blasberg, Ronald G.. "Synthesis and evaluation of [18F] labeled pyrimidine nucleosides for positron emission tomography imaging of herpes simplex virus 1 thymidine kinase gene expression". . p. 5377 - 5381. Retrieved 2007/10/03.