2-Chloro-9-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purin-6-aMine

Base Information

• Chemical Name: 2-Chloro-9-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purin-6-aMine
• CAS No.: 355138-50-0
• Molecular Formula: C24H19ClFN5O5
• Molecular Weight: 511.897
• Mol file: 355138-50-0.mol

Synonyms:2-Chloro-9-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purin-6-aMine;clofarabine-1

Chemical Property of 2-Chloro-9-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purin-6-aMine

Chemical Property:

• PSA: 131.45000
• LogP: 3.96120
• Storage Temp.: Refrigerator
• Solubility.: Acetonitrile, Chloroform, Methanol

Purity/Quality:

99%, ^*data from raw suppliers

6-Amino-2-chloro-9-(2''-deoxy-2-fluoro-3'',5''-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 6-Amino-2-chloro-9-(2''-deoxy-2-fluoro-3'',5''-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purine is an intermediate in the synthesis of N-[4-Amino-2-chloro-6-[(2-deoxy-2-fluoro-β-D-arabinopyranosyl)amino]-5-pyrimidinyl]-formamide which is a clofarabine related compound. Clofarabine (C586890) is a second generation purine nucleoside analog; antimetabolite that inhibits DNA synthesis and resists deamination by adenosine deaminase. Antineoplastic.

Technology Process of 2-Chloro-9-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purin-6-aMine

There total 20 articles about 2-Chloro-9-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purin-6-aMine 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: 85.0%

((2R,3R,4S,5R)-3-(benzoyloxy)-5-(2,6-dichloro-9H-purin-9-yl)-4-fluorotetrahydrofuran-2-yl)methyl benzoate (329187-80-6) → 6-amino-2-chloro-9-(2'-deoxy-2'-fluoro-3',5'-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purine (355138-50-0)

Guidance literature:

With ammonia; In acetonitrile; at 20 ℃; Solvent;

Reference yield: 66.0%

C25H19ClF3N5O8S → 6-amino-2-chloro-9-(2'-deoxy-2'-fluoro-3',5'-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purine (355138-50-0)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In ethyl acetate; at 70 ℃; for 24h;

DOI:10.1039/c6ra27790j

Reference yield: 60.0%

2-chloro-9-(3',5'-di-O-benzoyl-2'-O-trifluoromethylsulfonyl-β-D-ribofuranosyl)adenine (1353040-43-3) → 6-amino-2-chloro-9-(2'-deoxy-2'-fluoro-3',5'-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purine (355138-50-0)

Guidance literature:

With triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; In toluene; at 35 - 40 ℃; for 48h;

upstream raw materials:

((2R,3R,4S,5R)-3-(benzoyloxy)-5-(2,6-dichloro-9H-purin-9-yl)-4-fluorotetrahydrofuran-2-yl)methyl benzoate

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

9-Trimethylsilyl-2,6-dichlorpurin

2,6 dichloropurine

Downstream raw materials:

clofarabine

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine

(2R,3R,4S,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite

Refernces

• 1、 -. "A green synthetic clofarabine pharmaceutical intermediates (by machine translation)". . . Retrieved 2019/02/25.
• 2、 -. "METHOD FOR THE SYNTHESIS OF CLOFARABINE". . . Retrieved 2017/04/11.