Fazarabine

Base Information

• Chemical Name: Fazarabine
• CAS No.: 65886-71-7
• Molecular Formula: C₈H₁₂N₄O₅
• Molecular Weight: 244.207
• UNII: 5V71D8JOKK
• DSSTox Substance ID: DTXSID401024360
• Nikkaji Number: J33.115E
• Wikidata: Q27262921
• NCI Thesaurus Code: C1096
• ChEMBL ID: CHEMBL2106666
• Mol file: 65886-71-7.mol

Synonyms:1-beta-D-arabinosyl-5-azacytosine;5-azacytosine arabinoside;ara-5-aza-Cyd;ara-5-azacytosine;ara-AC;arabinofuranosyl-5-azacytosine;arabinosyl-5-azacytosine;fazarabine;NSC 281272;NSC-281272

Chemical Property of Fazarabine

Chemical Property:

• Vapor Pressure: 1.18E-13mmHg at 25°C
• Melting Point: 220 °C (decomp)
• Refractive Index: 1.823
• Boiling Point: 534.5 °C at 760 mmHg
• PKA: 13.46±0.70(Predicted)
• Flash Point: 277 °C
• PSA: 143.72000
• Density: 2.08g/cm³
• LogP: -2.58680
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 244.08076950
• Heavy Atom Count: 17
• Complexity: 384

Purity/Quality:

98%min ^*data from raw suppliers

FAZARABINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=NC(=O)N1C2C(C(C(O2)CO)O)O)N
• Isomeric SMILES: C1=NC(=NC(=O)N1[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O)N
• Uses: Antineoplastic.

Technology Process of Fazarabine

There total 7 articles about Fazarabine 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: 8.0%

1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-5-azacytosine (22432-98-0) → 5-azacytosine arabinoside (320-67-2,65886-71-7,114543-16-7) + 2-carbamoyl-1-formylguanidine

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal;

DOI:10.1135/cccc19960656

Reference yield:

5,6-dihydro-5-azacytidine hydrochloride (62402-31-7) → 5-azacytosine arabinoside (320-67-2,65886-71-7,114543-16-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / acetonitrile / 18 h / 40 - 50 °C

2: 83 percent / HCl / ethanol / 25 °C

3: 43 percent / 1 N NH₄OH / 6 h / Heating

4: 1.) BSTFA, O₂, 2.) Bu₄NF / 1.) acetonitrile, 30 h, reflux, 2.) THF

With hydrogenchloride; ammonium hydroxide; tetrabutyl ammonium fluoride; oxygen; N,O-Bis(trimethylsilyl)trifluoroacetamide; In ethanol; acetonitrile;

Reference yield:

5'-O-(2,5,5-trimethyl-1,3-dioxolan-4-on-2-yl)-3'-O-acetyl-3'-deoxy-5,6-dihydro-2,2'-anhydro-1-β-D-arabinofuranosyl-5-azacytosine hydrochloride → 5-azacytosine arabinoside (320-67-2,65886-71-7,114543-16-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / HCl / ethanol / 25 °C

2: 43 percent / 1 N NH₄OH / 6 h / Heating

3: 1.) BSTFA, O₂, 2.) Bu₄NF / 1.) acetonitrile, 30 h, reflux, 2.) THF

With hydrogenchloride; ammonium hydroxide; tetrabutyl ammonium fluoride; oxygen; N,O-Bis(trimethylsilyl)trifluoroacetamide; In ethanol;

upstream raw materials:

5,6-dihydro-1-β-D-arabinofuranosyl-5-azacytosine

1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-5-azacytosine

5,6-dihydro-5-azacytidine hydrochloride