[1-(6-Aminopurin-9-yl)-3-fluoropropan-2-yl]oxymethylphosphonic acid

Base Information

• Chemical Name: [1-(6-Aminopurin-9-yl)-3-fluoropropan-2-yl]oxymethylphosphonic acid
• CAS No.: 135295-27-1
• Molecular Formula: C₉H₁₃FN₅O₄P
• Molecular Weight: 305.205
• DSSTox Substance ID: DTXSID50928947
• Nikkaji Number: J472.265E
• Mol file: 135295-27-1.mol

Synonyms:3-FPMPA;9-(3-fluoro-2-phosphonylmethoxypropyl)adenine

Chemical Property of [1-(6-Aminopurin-9-yl)-3-fluoropropan-2-yl]oxymethylphosphonic acid

Chemical Property:

• Vapor Pressure: 1.31E-17mmHg at 25°C
• Boiling Point: 646.8°Cat760mmHg
• Flash Point: 344.9°C
• PSA: 146.19000
• Density: 1.86g/cm³
• LogP: 0.47960
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 305.06891907
• Heavy Atom Count: 20
• Complexity: 372

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)CC(CF)OCP(=O)(O)O)N

Technology Process of [1-(6-Aminopurin-9-yl)-3-fluoropropan-2-yl]oxymethylphosphonic acid

There total 6 articles about [1-(6-Aminopurin-9-yl)-3-fluoropropan-2-yl]oxymethylphosphonic acid 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: 65.0%

diethyl (1-(6-amino-9H-purin-9-yl)-3-fluoropropan-2-yloxy)methylphosphonate (1072094-99-5) → 9-(RS)-(3-fluoro-2-phosphonomethoxypropyl)adenine (135295-27-1)

Guidance literature:

diethyl (1-(6-amino-9H-purin-9-yl)-3-fluoropropan-2-yloxy)methylphosphonate; With trimethylsilyl bromide; In N,N-dimethyl-formamide;

With water; Further stages.;

DOI:10.1002/jlcr.1505

Reference yield:

1-(6-amino-9H-purin-9-yl)-3-fluoropropan-2-ol (138870-28-7) → 9-(RS)-(3-fluoro-2-phosphonomethoxypropyl)adenine (135295-27-1)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 1 h / Ambient temperature

2: pyridine / 2 h / Ambient temperature

3: ammonia / H₂O / 0.5 h / 0 °C

4: NaH / dimethylformamide / 1.) room temperature, 30 min, 2.) room temperature, 16 h; 80 deg C, 16 h

5: 1.) sodium methoxide, 2.) bromotrimethylsilane / 1.) methanol, room temperature, 16 h, 2.) acetonitrile, room temperature, 3 d

With trimethylsilyl bromide; ammonia; sodium methylate; sodium hydride; In pyridine; water; N,N-dimethyl-formamide;

DOI:10.1135/cccc19931645

Reference yield:

9-(3-Fluoro-2-trimethylsilanyloxy-propyl)-9H-purin-6-ylamine → 9-(RS)-(3-fluoro-2-phosphonomethoxypropyl)adenine (135295-27-1)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 2 h / Ambient temperature

2: ammonia / H₂O / 0.5 h / 0 °C

3: NaH / dimethylformamide / 1.) room temperature, 30 min, 2.) room temperature, 16 h; 80 deg C, 16 h

4: 1.) sodium methoxide, 2.) bromotrimethylsilane / 1.) methanol, room temperature, 16 h, 2.) acetonitrile, room temperature, 3 d

With trimethylsilyl bromide; ammonia; sodium methylate; sodium hydride; In pyridine; water; N,N-dimethyl-formamide;

DOI:10.1135/cccc19931645

upstream raw materials:

1-(6-amino-9H-purin-9-yl)-3-fluoropropan-2-ol

N⁶-benzoyl-9-(RS)-(3-fluoro-2-hydroxypropyl)adenine

diethyl (1-(6-amino-9H-purin-9-yl)-3-fluoropropan-2-yloxy)methylphosphonate

Refernces

• 1、 -. "SYNTHESIS OF OPTICALLY ACTIVE RADIO-LABELED REVERSE TRANSCRIPTASE INHIBITORS". Page/Page column 24. . Retrieved 2008/12/08.