2-Chloro-adenosine monophosphate

Base Information

• Chemical Name: 2-Chloro-adenosine monophosphate
• CAS No.: 21466-01-3
• Molecular Formula: C₁₀H₁₃ClN₅O₇P
• Molecular Weight: 381.669
• Nikkaji Number: J1.572.339D
• ChEMBL ID: CHEMBL3244493
• Mol file: 21466-01-3.mol

Synonyms:2-chloro-adenosine monophosphate;2-chloro-AMP

Chemical Property of 2-Chloro-adenosine monophosphate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 765.331°C at 760 mmHg
• Flash Point: 416.657°C
• PSA: 187.24000
• Density: 2.401g/cm³
• LogP: -0.13200
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Methanol; Water
• XLogP3: -2.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 381.0241125
• Heavy Atom Count: 24
• Complexity: 514

Purity/Quality:

98%Min ^*data from raw suppliers

2-Chloroadenosine 5??-Monophosphate Ditriethylamine Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=C(N=C(N=C2N1C3C(C(C(O3)COP(=O)(O)O)O)O)Cl)N
• Isomeric SMILES: C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)Cl)N
• Uses: 2-Chloro-5''-adenylic Acid is an intermediate for the synthesis of 2-Chloroadenosine Triphosphate Ammonium Salt (C364109). 2-Chloroadenosine Triphosphate is a P2Y purinoceptor agonist. A metabolite of 2-Chloroadenosine; an adenine nucleotide receptor.

Technology Process of 2-Chloro-adenosine monophosphate

There total 5 articles about 2-Chloro-adenosine 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: 37.0%

pentasodium 5-phosphoribosyl-α-1-pyrophosphate + 2-chloroadenine (1839-18-5) → phosphoric acid mono[(2R,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-ylmethyl]ester (21466-01-3)

Guidance literature:

With potassium dihydrogenphosphate; magnesium(II) chloride hexahydrate; recombinant Thermus thermophilus HB₂₇ adenine phosphoribosyltransferase; potassium hydroxide; In water; at 75 ℃; for 48h; pH=8; Temperature; Catalytic behavior; Enzymatic reaction;

DOI:10.3762/bjoc.14.289

Reference yield:

Phosphoric acid (3aR,4R,6R,6aR)-6-(6-amino-2-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester di-tert-butyl ester → phosphoric acid mono[(2R,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-ylmethyl]ester (21466-01-3)

Guidance literature:

With DOWEX 50WX₈-200; In methanol; water;

DOI:10.1021/jm010538v

Reference yield:

((3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (24639-06-3) → phosphoric acid mono[(2R,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-ylmethyl]ester (21466-01-3)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrazole / tetrahydrofuran

2: m-CPBA / tetrahydrofuran; CH₂Cl₂

3: DOWEX 50Wx₈-200 / H₂O; methanol

With 1H-tetrazole; DOWEX 50WX₈-200; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jm010538v

upstream raw materials:

((3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

2-chloroadenine

Downstream raw materials:

2-chloroadenosine-5'-diphosphate