(S)-(((1-(6-Amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonic acid

Base Information

• Chemical Name: (S)-(((1-(6-Amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonic acid
• CAS No.: 147127-19-3
• Molecular Formula: C9H14 N5 O4 P
• Molecular Weight: 287.2123
• Hs Code.: 2933990090
• Nikkaji Number: J540.141K
• ChEMBL ID: CHEMBL483891
• Mol file: 147127-19-3.mol

Synonyms:147127-19-3;(S)-(((1-(6-Amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonic acid;(S)-Tenofovir;(S)-PMPA;(S)-TDF;(S)-9-(2-Phosphonylmethoxypropyl)adenine;[(2S)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethylphosphonic acid;({[(2S)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid;C9H14N5O4P;Phosphonic acid, (((1S)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy)methyl)-;MFCD21604708;Phosphonic acid, [[(1S)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl]-;CHEMBL483891;SCHEMBL2040329;AMY11188;(S)-(((1-(6-Amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonicacid;AKOS016844118;HY-W074930;(S)-GS 1278;Phosphonic acid, P-[[(1S)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl]-;AS-73240;(s)-9-[2-(phosphonomethoxy)propyl]adenine;CS-0111892;O10188;EN300-7420358;J-008317;[(1S)-2-(6-aminopurin-9-yl)-1-methyl-ethoxy]methylphosphonic acid

Chemical Property of (S)-(((1-(6-Amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonic acid

Chemical Property:

• Vapor Pressure: 4.92E-16mmHg at 25°C
• Melting Point: >260°C (dec.)
• Boiling Point: 616.1°Cat760mmHg
• PKA: 2.36±0.10(Predicted)
• Flash Point: 326.4°C
• PSA: 146.19000
• Density: 1.79g/cm³
• LogP: 0.53000
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 287.07834094
• Heavy Atom Count: 19
• Complexity: 354

Purity/Quality:

99.0% ^*data from raw suppliers

(S)-Tenofovir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CN1C=NC2=C(N=CN=C21)N)OCP(=O)(O)O
• Isomeric SMILES: C[C@@H](CN1C=NC2=C(N=CN=C21)N)OCP(=O)(O)O
• Uses: (S)-Tenofovir is an S-enatiomeric derivative of Tenofovir (T018500). (S)-Tenofovir displays virucidal activity against herpes, visna virus and retrovirus. The S enantiomer of Tenofovir (T018500) is less effective against HIV than their (R)-enantiomeric counterparts.

Technology Process of (S)-(((1-(6-Amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonic acid

There total 15 articles about (S)-(((1-(6-Amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonic 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: 88.0%

methyl hydrogen ({[1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonate (123155-85-1) → (+/-)-0-(2-phosphonylmethoxypropyl)adenine (121149-89-1,147127-19-3,147127-20-6,107021-12-5)

Guidance literature:

With trimethylsilyl iodide; In N,N-dimethyl-formamide; for 16h; Ambient temperature;

Reference yield: 88.0%

diethyl (p-toluenesulfonyloxymethane)phosphonate (31618-90-3) + (R)-9-(2-hydroxypropyl)adenine (14047-28-0,712-00-5) → (S)-9-(2-phosphonylmethoxypropyl)adenine (147127-19-3)

Guidance literature:

(R)-9-(2-hydroxypropyl)adenine; With bis(isopropoxy) magnesium; In N,N-dimethyl-formamide; at 65 ℃; for 1h; Inert atmosphere;

diethyl (p-toluenesulfonyloxymethane)phosphonate; In N,N-dimethyl-formamide; at 45 - 55 ℃; for 10h;

With hydrogenchloride; In water; at 90 ℃; for 10h;

Reference yield: 77.0%

bis(2-propyl) (S)-9-(2-phosphonomethoxypropyl)adenine (173277-57-1) → (S)-9-(2-phosphonylmethoxypropyl)adenine (147127-19-3)

Guidance literature:

With trimethylsilyl bromide; In acetonitrile; Ambient temperature;

DOI:10.1135/cccc19951390

upstream raw materials:

methyl hydrogen ({[1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonate

N'-[9-(2-Hydroxy-propyl)-9H-purin-6-yl]-N,N-dimethyl-formamidine

6-amino-α-methyl-9H-purine-9-ethanol

6-chloro-7H-purine

Downstream raw materials:

((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphoric acid monophenyl ester

(S)-PMPAp

Refernces

• 1、 -. "Tenofovirpurification method". Paragraph 0047-0049; 0064. . Retrieved 2020/01/25.
• 2、 Holy, Antonin,Dvorakova, Hana,Masojidkova, Milena. "SYNTHESIS OF ENANTIOMERIC N-(2-PHOSPHONOMETHOXYPROPYL)DERIVATIVES OF PURINE AND PYRIMIDINE BASES. II. THE SYNTHON APPROACH". . p. 1390 - 1409. Retrieved 2007/10/02.