355138-50-0

Basic information

• Product Name: 2-Chloro-9-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purin-6-aMine
• Synonyms: 2-Chloro-9-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purin-6-aMine;clofarabine-1
• CAS NO: 355138-50-0
• Molecular Formula: C₂₄H₁₉ClFN₅O₅
• Molecular Weight: 511.8895632
• Mol File: 355138-50-0.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Acetonitrile, Chloroform, Methanol
• CAS DataBase Reference: 2-Chloro-9-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purin-6-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-9-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purin-6-aMine(355138-50-0)
• EPA Substance Registry System: 2-Chloro-9-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purin-6-aMine(355138-50-0)

Safety Data

• Hazardous Substances Data: 355138-50-0(Hazardous Substances Data)

Usage

Description

2-Chloro-9-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purin-6-aMine is a complex organic compound that serves as an intermediate in the synthesis of clofarabine-related compounds. It is characterized by its unique molecular structure, which includes a purine base with a chloro and amino substitution, as well as a modified sugar moiety. 2-Chloro-9-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purin-6-aMine plays a crucial role in the development of novel antineoplastic agents.

Uses

Used in Pharmaceutical Industry:
2-Chloro-9-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purin-6-aMine is used as an intermediate in the synthesis of clofarabine, a second-generation purine nucleoside analog. Clofarabine is an antineoplastic agent that inhibits DNA synthesis and resists deamination by adenosine deaminase, making it a valuable tool in the fight against cancer.
2-Chloro-9-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purin-6-aMine's role in the synthesis of clofarabine is significant because it contributes to the development of a potent antimetabolite with potential applications in the treatment of various types of cancer. By serving as a key intermediate, this compound enables the creation of new therapeutic options for patients in need.

Upstream product

• 329187-80-6 ((2R,3R,4S,5R)-3-(benzoyloxy)-5-(2,6-dichloro-9H-purin-9-yl)-4-fluorotetrahydrofuran-2-yl)methyl benzoate 
• 97614-43-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose 
• 75788-35-1 9-Trimethylsilyl-2,6-dichlorpurin 
• 5451-40-1 2,6 dichloropurine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 1839-18-5 2-chloroadenine 
• 1353040-42-2 2-chloro-9-(3',5'-di-O-benzoyl-β-D-ribofuranosyl)adenine 
• 1055168-98-3 6-amino-2-chloro-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine 
• 1353040-43-3 2-chloro-9-(3',5'-di-O-benzoyl-2'-O-trifluoromethylsulfonyl-β-D-ribofuranosyl)adenine 
• 97614-44-3 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide 
• 146-77-0 2-Chloroadenosine 
• 118-00-3 G 
• 58-96-8 uridine 
• 98855-71-1 ((2R,3R,4S)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate 

Downstream Products

• 123318-82-1 clofarabine 
• 20187-82-0 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine 
• 136834-22-5 (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 

Relevant articles and documents

A green synthetic clofarabine pharmaceutical intermediates (by machine translation)

The invention relates to a green synthetic clofarabine medical intermediates, in particular comprises the following steps: The formula II compound is dissolved in the organic solvent, under ice bath by adding 40% of the hydrobromic, tetrabutyl ammonium fluoride, stirring for 3 hours, adding triethylamine three [...], continuing to stir 2 - 3 hours, [...] I compound. (by machine translation)

Method for synthesizing clofarabine

The invention discloses a method for synthesizing clofarabine; the method comprises the following synthetic routes described in the specification, wherein in the formula III and the formula IV, R1 and R2 are the same or different acyl groups. The method comprises the following steps: 1) ammoniation: dissolving a compound represented by the formula III in an organic solvent, introducing ammonia gas, and carrying out a closed reaction, to obtain a compound represented by the formula IV after the reaction is completed, wherein the organic solvent is any combination of one or two or more of acetonitrile, ethyl acetate, dichloromethane and tetrahydrofuran, the concentration of ammonia gas dissolved in the organic solvent is 0.1-20 wt%, the closed reaction is carried out for 10-40 hours, and the reaction temperature is 0-100 DEG C; and 2) protecting group removal: dissolving the compound represented by the formula IV and prepared in the step 1) in alcohol, adding an alcohol solution of sodium alkoxide, carrying out a reaction, then adjusting the pH value to 6-7, cooling and crystallizing, and thus obtaining a clofarabine crude product.

Stereoselective synthesis of 2′-modified nucleosides by using ortho-alkynyl benzoate as a gold(i)-catalyzed removable neighboring participation group

In the present paper, we report a novel strategy for highly efficient stereoselective synthesis of 2′-modified nucleosides by using ortho-alkynyl benzoate as neighboring participation group. Subsequently, ortho-alkynyl benzoate can be removed smoothly in the presence of 5 mol% Ph3PAuCl-AgOTf in dichloromethane with H2O (1 eq.) and ethanol (6 eq.) to afford 2′-OH nucleosides in high yields and selectivity.