9-[(2R)-2-(diphenoxyphosphorylmethoxy)propyl]purin-6-amine

Base Information

• Chemical Name: 9-[(2R)-2-(diphenoxyphosphorylmethoxy)propyl]purin-6-amine
• CAS No.: 342631-41-8
• Molecular Formula: C₂₁H₂₂N₅O₄P
• Molecular Weight: 439.411
• UNII: G2GN8Y38TV
• ChEMBL ID: CHEMBL9954
• Mol file: 342631-41-8.mol

Synonyms:342631-41-8;DIPHENYL (R)-(((1-(6-AMINO-9H-PURIN-9-YL)PROPAN-2-YL)OXY)METHYL)PHOSPHONATE;9-[(2R)-2-(diphenoxyphosphorylmethoxy)propyl]purin-6-amine;G2GN8Y38TV;(R)-Diphenyl (((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate;Phosphonic acid, (((1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy)methyl)-, diphenyl ester;UNII-G2GN8Y38TV;CHEMBL9954;SCHEMBL17204381;Tenofovir Alafenamide Impurity 1;AMY11191;CS-0164428;F19321;A936611;(R)-Diphenyl(((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate;(R)-diphenyl (((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate? (tenofovir Impurity pound(c);Phosphonic acid, [[[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethyl]oxy]methyl]-, diphenyl ester

Chemical Property of 9-[(2R)-2-(diphenoxyphosphorylmethoxy)propyl]purin-6-amine

Chemical Property:

• Boiling Point: 636.3±65.0 °C(Predicted)
• PKA: 4.21±0.10(Predicted)
• Density: 1.39±0.1 g/cm3(Predicted)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 439.14094120
• Heavy Atom Count: 31
• Complexity: 578

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-Diphenyl(((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CN1C=NC2=C(N=CN=C21)N)OCP(=O)(OC3=CC=CC=C3)OC4=CC=CC=C4
• Isomeric SMILES: C[C@H](CN1C=NC2=C(N=CN=C21)N)OCP(=O)(OC3=CC=CC=C3)OC4=CC=CC=C4
• Uses: (R)-Diphenyl (((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate is a reagent for the synthesis of amidate prodrugs of PMEA and PMPA. Also functions as a reagent in the preparation of tenofovir alafenamide fumarate impurity.

Technology Process of 9-[(2R)-2-(diphenoxyphosphorylmethoxy)propyl]purin-6-amine

There total 5 articles about 9-[(2R)-2-(diphenoxyphosphorylmethoxy)propyl]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: 91.9%

6-amino-9-[(2R)-2-(dichlorophosphorylmethoxy)propyl]purine + phenol (108-95-2,27073-41-2) → 9-[(R)-2-[[(S)-[bis(phenoxy)phosphinyl]]methoxy]propyl]adenine (342631-41-8)

Guidance literature:

In acetonitrile; at 0 - 25 ℃; for 16h; Inert atmosphere;

Reference yield: 85.0%

tenofovir (147127-20-6) + phenol (108-95-2,27073-41-2) → 9-[(R)-2-[[(S)-[bis(phenoxy)phosphinyl]]methoxy]propyl]adenine (342631-41-8)

Guidance literature:

tenofovir; With thionyl chloride; In acetonitrile; at 70 ℃; for 2h; Inert atmosphere; Large scale;

phenol; In acetonitrile; at 80 ℃; for 13h; Large scale;

Reference yield: 70.3%

((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphoric acid monophenyl ester (379270-35-6) + phenol (108-95-2,27073-41-2) → 9-[(R)-2-[[(S)-[bis(phenoxy)phosphinyl]]methoxy]propyl]adenine (342631-41-8)

Guidance literature:

((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphoric acid monophenyl ester; With thionyl chloride; In acetonitrile; at 70 ℃;

phenol; In acetonitrile; at -5 ℃; for 1h;

upstream raw materials:

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

phenol

tenofovir

Downstream raw materials:

(R)-diethyl (((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate

tenofovir disoproxil

Refernces

• 1、 -. "Preparation method of high-purity tenofovir alafenamide impurity TAF-Y". Paragraph 0040; 0041; 0042; 0043; 0044; 0045. . Retrieved 2019/02/10.
• 2、 -. "Method of preparing nucleoside analogs and intermediates thereof which has advantages of high reaction yield, high product purity, convenient post-treatment, and suitable for industrial mass production". . . Retrieved 2017/09/26.