9-[2-[[(4S)-4-(3-chlorophenyl)-2-oxo-1,3,2lambda5-dioxaphosphinan-2-yl]methoxy]ethyl]purin-6-amine

Base Information

• Chemical Name: 9-[2-[[(4S)-4-(3-chlorophenyl)-2-oxo-1,3,2lambda5-dioxaphosphinan-2-yl]methoxy]ethyl]purin-6-amine
• CAS No.: 625095-60-5
• Molecular Formula: C17H19ClN5O4P
• Molecular Weight: 423.796
• NCI Thesaurus Code: C66453
• Nikkaji Number: J2.048.989H
• Mol file: 625095-60-5.mol

Synonyms:hepavir-B;ICN 2001-3;ICN-2001-3;ICN2001-3;MB 06866;MB-06866;MB-6866;MB06866;pradefovir;pradefovir mesylate;remofovir;remofovir mesylate

Chemical Property of 9-[2-[[(4S)-4-(3-chlorophenyl)-2-oxo-1,3,2lambda5-dioxaphosphinan-2-yl]methoxy]ethyl]purin-6-amine

Chemical Property:

• Boiling Point: 649.7±65.0 °C(Predicted)
• PKA: 4.21±0.10(Predicted)
• PSA: 124.19000
• Density: 1.62±0.1 g/cm3(Predicted)
• LogP: 3.98850
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 423.0863188
• Heavy Atom Count: 28
• Complexity: 576

Purity/Quality:

97% ^*data from raw suppliers

Pradefovir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COP(=O)(OC1C2=CC(=CC=C2)Cl)COCCN3C=NC4=C(N=CN=C43)N
• Isomeric SMILES: C1COP(=O)(O[C@@H]1C2=CC(=CC=C2)Cl)COCCN3C=NC4=C(N=CN=C43)N
• Uses: Antiviral. Pradefovir is a prodrug that targets Adefovir (A247500) to liver for the treatment of hepatitis B.

Technology Process of 9-[2-[[(4S)-4-(3-chlorophenyl)-2-oxo-1,3,2lambda5-dioxaphosphinan-2-yl]methoxy]ethyl]purin-6-amine

There total 12 articles about 9-[2-[[(4S)-4-(3-chlorophenyl)-2-oxo-1,3,2lambda5-dioxaphosphinan-2-yl]methoxy]ethyl]purin-6-amine 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:

9-{2-[2,4-cis-(S)-(+)-4-(3'-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]metboxyethyl}adenine methanesulfonate (625095-61-6) → (+)-cis-9-{2-[4-(S)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-methyleneoxy]eth-1-yl}adenine (625095-60-5)

Guidance literature:

With sodium hydrogencarbonate; In water; Heating / reflux;

Reference yield:

C22H28ClN6O4P → (+)-cis-9-{2-[4-(S)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-methyleneoxy]eth-1-yl}adenine (625095-60-5)

Guidance literature:

With acetic acid; In ethanol; for 8h; Heating / reflux;

Reference yield:

9-{2-[2,4-trans(R)-(-)-4-(3-Chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]methoxyethyl}adenine + C22H28ClN6O4P → C17H19ClN5O4P (625095-66-1) + (+)-cis-9-{2-[4-(S)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-methyleneoxy]eth-1-yl}adenine (625095-60-5)

Guidance literature:

With acetic acid; In ethanol; for 8h; Heating / reflux;

upstream raw materials:

3-(3-chlorophenyl)-3-oxopropanoic acid

Adefovir

m-Chlorobenzaldehyde

(S)-(-)-1-(3-Chlorophenyl)-1,3-propanediol

Downstream raw materials:

9-{2-[2,4-cis(S)-(+)-4-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]methoxyethyl}adenine maleate

9-{2-[2,4-cis-(S)-(+)-4-(3'-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]metboxyethyl}adenine methanesulfonate

CH₄O₃S*C₁₇H₁₉ClN₅O₄P

Refernces

• 1、 -. "LEWIS ACID MEDIATED SYNTHESIS OF CYCLIC ESTERS". Page/Page column 30. . Retrieved 2008/06/13.
• 2、 -. "Novel phosphonic acid based prodrugs of PMEA and its analogues". Page 22. . Retrieved 2010/11/30.