Cytosine arabinoside monophosphate

Base Information

• Chemical Name: Cytosine arabinoside monophosphate
• CAS No.: 7075-11-8
• Molecular Formula: C9H14 N3 O8 P
• Molecular Weight: 323.199
• Hs Code.: 29349990
• NSC Number: 120953,99445
• DSSTox Substance ID: DTXSID70861605
• ChEMBL ID: CHEMBL296272
• Mol file: 7075-11-8.mol

Synonyms:Acid, Polycytidylic;Acids, Polycytidylic;Cytosine Polynucleotides;Poly C;Polycytidylic Acid;Polycytidylic Acids;Polynucleotides, Cytosine

Chemical Property of Cytosine arabinoside monophosphate

Chemical Property:

• Melting Point: 169-174°C
• Boiling Point: 678.1±65.0 °C(Predicted)
• PKA: 1.86±0.10(Predicted)
• Flash Point: 363.9oC
• PSA: 187.17000
• Density: 2.15±0.1 g/cm3(Predicted)
• LogP: -1.86480
• Storage Temp.: −20°C
• Solubility.: Aqueous Base (Slightly)
• XLogP3: -3.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 323.05185141
• Heavy Atom Count: 21
• Complexity: 531

Purity/Quality:

97% ^*data from raw suppliers

Cytarabine5’-Monophosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 22-36-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)N=C1N)C2C(C(C(O2)COP(=O)(O)O)O)O
• Recent ClinicalTrials: CMP vs Fascia Iliaca Block
• Uses: A derivative of Cytarabine, a potent cytotoxic-antiviral nucleoside. A derivative of Cytarabine, a potent cytotoxic-antiviral nucleoside

Technology Process of Cytosine arabinoside monophosphate

There total 16 articles about Cytosine arabinoside monophosphate 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: 60.0%

arabinosyl cytosine (147-94-4) → cytosine arabinoside-5'-monophosphate (7075-11-8,30811-80-4)

Guidance literature:

With triethyl phosphate; trichlorophosphate; at 0 ℃; for 22h;

DOI:10.1021/jm9603680

Reference yield:

→ L-cytidine-5'-monophosphate (63-37-6,3083-49-6,7075-11-8,20263-52-9,21138-23-8,22257-03-0,22257-04-1,22257-05-2,27921-79-5,56943-04-5,30811-80-4)

Guidance literature:

Cytidin 2f, 'Phosphat' I;

Reference yield:

→ [5']cytidylic acid (63-37-6,3083-49-6,7075-11-8,20263-52-9,21138-23-8,22257-03-0,22257-04-1,22257-05-2,27921-79-5,56943-04-5,30811-80-4)

Guidance literature:

2',3'-O-Isopropyliden-cytidin, (HO)2P(O)H/Hg2+/1-Methyl-imidazol;

upstream raw materials:

1-β-D-arabinofuranosylcytosine 5'-(n-octyl phosphate)

Phosphoric acid (2R,3S,4S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester propyl ester

1-β-D-arabinofuranosylcytosine 3',5'-diphosphate

arabinosyl cytosine

Downstream raw materials:

arabinosyl cytosine

arabinosyluracil-5'-monophosphate

4-amino-1-[O⁵-(hydroxy-phenoxy-phosphoryl)-β-D-arabinofuranosyl]-1H-pyrimidin-2-one

Refernces

• 1、 Abraham, Timothy W.,Kalman, Thomas I.,McIntee, Edward J.,Wagner, Carston R.. "Synthesis and biological activity of aromatic amino acid phosphoramidates of 5-fluoro-2'-deoxyuridine and 1-β- arabinofuranosylcytosine: Evidence of phosphoramidase activity". . p. 4569 - 4575. Retrieved 2007/10/03.
• 2、 Saneyoshi,Morozumi,Kodama,Machida,Kuninaka,Yoshino. "Synthetic nucleosides and nucleotides. XVI. Synthesis and biological evaluations of a series of 1-β-d-arabinofuranosyl-cystosine 5'-alkyl or arylphosphates". . p. 2915 - 2923. Retrieved 2007/10/02.