ap-dCTP

Base Information

• Chemical Name: ap-dCTP
• CAS No.: 115899-39-3
• Molecular Formula: C12H19N4O13P3
• Molecular Weight: 520.22
• DSSTox Substance ID: DTXSID201144677
• Nikkaji Number: J2.064.528H
• Mol file: 115899-39-3.mol

Synonyms:ap-dCTP;5-Propargylamino-dCTP;115899-39-3;[[(2R,3S,5R)-5-[4-amino-5-(3-aminoprop-1-ynyl)-2-oxopyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate;Cytidine 5'-(tetrahydrogen triphosphate), 5-(3-amino-1-propyn-1-yl)-2'-deoxy-;SCHEMBL5664002;DTXSID201144677;AKOS024464464;HY-132142;CS-0149518;5-(3-Amino-1-propyn-1-yl)-2'-deoxycytidine 5'-(tetrahydrogen triphosphate)

Chemical Property of ap-dCTP

Chemical Property:

• Boiling Point: 836.0±75.0 °C(Predicted)
• PKA: 0.97±0.50(Predicted)
• Density: 2.16±0.1 g/cm3(Predicted)
• XLogP3: -8.5
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 9
• Exact Mass: 520.01614767
• Heavy Atom Count: 32
• Complexity: 1030

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=NC2=O)N)C#CCN)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=NC2=O)N)C#CCN)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O

Technology Process of ap-dCTP

There total 5 articles about ap-dCTP 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:

C14H18F3N4O14P3 → 5-[3-aminoprop-1-ynyl]-2'-deoxycytidine-5'-O-triphosphate (115899-39-3)

Guidance literature:

With ammonium hydroxide; at 20 ℃; for 4h;

DOI:10.1021/ja051725b

Reference yield:

5-(3-Trifluoroacetamido-1-propynyl)-2'-deoxycytidine (115899-38-2) + tri-n-butylamine pyrophosphate → 5-[3-aminoprop-1-ynyl]-2'-deoxycytidine-5'-O-triphosphate (115899-39-3)

Guidance literature:

tri-n-butylamine pyrophosphate; With 2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one; tributyl-amine; C₆₉H₇₇N₁₄O₂₃P₃S₄; iodine; In N,N-dimethyl-formamide; for 1h;

5-(3-Trifluoroacetamido-1-propynyl)-2'-deoxycytidine; With pyridine; In water; N,N-dimethyl-formamide; for 2h;

Reference yield:

5-Iodo-2'-deoxycytidine (611-53-0) → 5-[3-aminoprop-1-ynyl]-2'-deoxycytidine-5'-O-triphosphate (115899-39-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 76 percent / CuI; triethylamine; Pd(PPh₃)4 / dimethylformamide / 3.5 h / 20 °C

2.1: POCl₃; H₂O; pyridine / acetonitrile / 24 h / -25 °C

2.2: (nBu₃NH)2H₂P₂O₇; nBu₃N / acetonitrile; dimethylformamide / 0.08 h / 0 °C

2.3: aq. triethylammonium bicarbonate / acetonitrile; dimethylformamide / 1 h / 0 - 20 °C

3.1: aq. NH₃ / 4 h / 20 °C

With pyridine; ammonium hydroxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; triethylamine; trichlorophosphate; In N,N-dimethyl-formamide; acetonitrile; 1.1: Sonogashira coupling;

DOI:10.1021/ja051725b

upstream raw materials:

5-Iodo-2'-deoxycytidine

5-(3-Trifluoroacetamido-1-propynyl)-2'-deoxycytidine

Refernces

• 1、 -. "Synthesis of acid-sensitive connection unit and its use in DNA sequencing". Paragraph 0443; 0452; 0457; 0458. . Retrieved 2018/02/04.