alamifovir

Base Information

• Chemical Name: alamifovir
• CAS No.: 193681-12-8
• Molecular Formula: C19H20 F6 N5 O5 P S
• Molecular Weight: 575.428
• Mol file: 193681-12-8.mol

Synonyms:Phosphonic acid,[[2-[2-amino-6-[(4-methoxyphenyl)thio]-9H-purin-9-yl]ethoxy]methyl]-,bis(2,2,2-trifluoroethyl) ester (9CI); Alamifovir; LY 582563; MCC 478

Chemical Property of alamifovir

Chemical Property:

• Vapor Pressure: 4.51E-16mmHg at 25°C
• Melting Point: 84-85℃
• Boiling Point: 635.9°Cat760mmHg
• PKA: 2?+-.0.10(Predicted)
• Flash Point: 338.4°C
• PSA: 158.72000
• Density: 1.61g/cm³
• LogP: 5.47450

Purity/Quality:

99% ^*data from raw suppliers

ALAMIFOVIR 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of alamifovir

There total 10 articles about alamifovir 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: 71.0%

4-Methoxybenzenethiol (696-63-9) + 2-amino-6-chloro-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester (186345-42-6) → Alamifovir (193681-12-8)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 100 ℃; for 2h;

DOI:10.1021/jm020036x

Reference yield: 42.0%

2-amino-6-[(4-methoxyphenyl)sulfanyl]purine + bis(trifluoroethyl) (2-iodoethoxymethyl)phosphonate (186345-41-5) → Alamifovir (193681-12-8)

Guidance literature:

2-amino-6-[(4-methoxyphenyl)sulfanyl]purine; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 80 ℃; for 1h;

bis(trifluoroethyl) (2-iodoethoxymethyl)phosphonate; In N,N-dimethyl-formamide; at 100 ℃;

DOI:10.1016/j.bmc.2004.10.007

Reference yield:

bis(2,2,2-trifluoroethyl) [(2-chloroethoxy)methyl]phosphonate (186345-40-4) → Alamifovir (193681-12-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 80 percent / NaI

2.1: DBU / dimethylformamide / 1 h / 80 °C

2.2: 42 percent / dimethylformamide / 100 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2004.10.007

upstream raw materials:

4-Methoxybenzenethiol

2-amino-6-chloro-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester

bis(trifluoroethyl) (2-iodoethoxymethyl)phosphonate

2-[bis(tert-butoxycarbonyl)amino]-6-chloro-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester

Refernces

• 1、 Wang, Ji-Quan,Fei, Xiangshu,Gardner, Thomas A.,Hutchins, Gary D.,Zheng, Qi-Huang. "Synthesis of 2-amino-6-(4-[11C]methoxyphenylthio)-9-[2- (phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester as a novel potential PET gene reporter probe for HBV and HSV-tk in cancers". . p. 549 - 556. Retrieved 2007/10/03.