1-beta-D-Arabinofuranosylcytosine triacetate

Base Information

• Chemical Name: 1-beta-D-Arabinofuranosylcytosine triacetate
• CAS No.: 6742-07-0
• Molecular Formula: C15H19N3O8
• Molecular Weight: 369.331
• NSC Number: 93150
• DSSTox Substance ID: DTXSID60874683
• Mol file: 6742-07-0.mol

Synonyms:Ara-C triacetate;Cytosine arabinoside triacetate;NSC-93150;6742-07-0;2',3',5'-TRI-O-ACETYLCYTIDINE;SCHEMBL2238447;DTXSID60874683;Cytidine, 2',3',5'-triacetate;BCP31756;NSC93150;NSC 93150;1-.beta.-D-Arabinofuranosylcytosine triacetate;WLN: T6NVNJ DZ A- BT5OTJ COV1 DOV1 E1OV1;1-.beta.-D-Arabinofuranosylcytosine,3',5'-triacetate;2(1H)-PYRIMIDINONE, 4-AMINO-1-(2,3,5-TRI-O-ACETY;2(1H)-Pyrimidinone,3,5-tri-O-acetyl-.beta.-D-arabinofuranosyl)-

Chemical Property of 1-beta-D-Arabinofuranosylcytosine triacetate

Chemical Property:

• Vapor Pressure: 2.04E-10mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Boiling Point: 507.4°Cat760mmHg
• Flash Point: 260.6°C
• PSA: 149.04000
• Density: 1.52g/cm³
• LogP: -0.26940
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 369.11721457
• Heavy Atom Count: 26
• Complexity: 674

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(O1)N2C=CC(=NC2=O)N)OC(=O)C)OC(=O)C

Technology Process of 1-beta-D-Arabinofuranosylcytosine triacetate

There total 9 articles about 1-beta-D-Arabinofuranosylcytosine triacetate 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: 90.0%

2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl-4-thiouridine (25130-27-2) → 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)cytosine (6742-07-0)

Guidance literature:

With ammonia; 3,3-dimethyldioxirane; In dichloromethane; acetone; at 25 ℃;

DOI:10.1016/0040-4020(96)00289-X

Reference yield:

cytarabine hydrochloride (69-74-9,29363-79-9) → 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)cytosine (6742-07-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 129 g / pyridine / 18 h / 45 °C

2: ZnBr₂ / CHCl₃; methanol / Ambient temperature

With pyridine; zinc dibromide; In methanol; chloroform;

DOI:10.1021/jm00394a039

Reference yield:

4-(1,2,4-triazol-1-yl)-1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)pyrimidine-2(1H)one (82855-62-7) → 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)cytosine (6742-07-0)

Guidance literature:

With ammonium hydroxide; In 1,4-dioxane; for 6h; Ambient temperature;

DOI:10.1039/P19820001171

upstream raw materials:

4-(1,2,4-triazol-1-yl)-1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)pyrimidine-2(1H)one

2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl-4-thiouridine

cytarabine hydrochloride

2,2'-Anhydrouridine

Downstream raw materials:

arabinosyl cytosine

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