ChemicalBook CAS DataBase List Clofarabine

Clofarabine synthesis

12synthesis methods

Product Name:Clofarabine
CAS Number:123318-82-1
Molecular formula:C10H11ClFN5O3
Molecular Weight:303.68

Clofarabine is a second generation purine nucleoside analog with antineoplastic activity. Clofarabine is phosphorylated intracellularly to the cytotoxic active 5'-triphosphate metabolite, which inhibits the enzymatic activities of ribonucleotide reductase and DNA polymerase, resulting in inhibition of DNA repair and synthesis of DNA and RNA. This nucleoside analog also disrupts mitochondrial function and membrane integrity, resulting in the release of pre-apoptotic factors, including cytochrome C and apoptotic-inducing factor, which activate apoptosis.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

ROUTE 9

Cen, Yana; Sauve, Anthony A. Efficient Syntheses of Clofarabine and Gemcitabine From 2-Deoxyribonolactone. Nucleosides, Nucleotides & Nucleic Acids. Department of Pharmacology. Weill Medical College of Cornell University. New York, USA. Volume 29. Issue 2. Pages 113-122. 2010

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

355138-50-0
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123318-82-1
414 suppliers
$7.00/10mg

Yield:123318-82-1 95.41%

Reaction Conditions:

with methanol;sodium methylate at 15 - 20; for 2 h;

Steps:

2

The last step intermediate obtained clofarabine added 10mL of anhydrous methanol,After stirring, NaOCH3 / CH3OH solution (193.41mg dissolved in 2mL anhydrous methanol) was added, and the mixture was stirred at 15-20 for 2h. The reaction was complete by TLC. After completion of the reaction, the insoluble matter was removed by filtration, and a large amount of solid was precipitated from the filtrate. The pH was adjusted to 6.5 to 7.5 by adding acetic acid under stirring. After adjustment, the mixture was stirred at room temperature for 30 minutes, filtered and the cake was washed with a small amount of cold methanol to obtain clofarabine, which was vacuum dried at 50C to obtain 1.73 g of clofarabine product in a yield of 95.41%. Result of liquid phase: 99.85%.

References:

CN105601688,2016,A Location in patent:Paragraph 0049- 0058

1234346-14-5
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123318-82-1
414 suppliers
$7.00/10mg

References

1839-18-5
362 suppliers
$10.00/1g

1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil

69123-94-0
162 suppliers
$60.00/1g

123318-82-1
414 suppliers
$7.00/10mg

References

97614-43-2 Synthesis

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

97614-43-2
334 suppliers
$5.00/250mg

123318-82-1
414 suppliers
$7.00/10mg

References

2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate

97614-44-3
68 suppliers
$45.00/100mg

123318-82-1
414 suppliers
$7.00/10mg

References

Clofarabine Related Search:

Ursodeoxycholic acid 6-Aminocaproic acid Glycine Chenodeoxycholic acid Fludarabine phosphate Tris(hydroxymethyl)nitromethane Capecitabine Cladribine Fluorine 1,3,5-Tri-O-benzoyl-D-ribofuranose