N-((R)-(((1R)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy)methyl)phenoxyphosphinyl)-L-alanine 1-methylethyl ester

Base Information

Chemical Name:N-((R)-(((1R)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy)methyl)phenoxyphosphinyl)-L-alanine 1-methylethyl ester
CAS No.:383365-04-6
Molecular Formula:C21H29N6O5P
Molecular Weight:476.472
Hs Code.:
UNII:J4414G3BUK
Wikipedia:Tenofovir_alafenamide
Mol file:383365-04-6.mol

Synonyms:GS-7340;GS-734003;L-alanine, N-((S)-(((1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy)methyl)phenoxyphosphinyl)-, 1-methylethyl ester;tenofovir alafenamide;vemlidy

Suppliers and Price of N-((R)-(((1R)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy)methyl)phenoxyphosphinyl)-L-alanine 1-methylethyl ester

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
N-[(R)-[[(1R)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy]methyl]phenoxyphosphinyl]-L-alanine1-MethylethylEster
5mg
$ 925.00

Total 19 raw suppliers

Chemical Property of N-((R)-(((1R)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy)methyl)phenoxyphosphinyl)-L-alanine 1-methylethyl ester

Chemical Property:

Boiling Point:640.4±65.0 °C(Predicted)
PKA:4.21±0.10(Predicted)
PSA：153.29000
Density:1.39±0.1 g/cm3(Predicted)
LogP:3.94500
XLogP3:1.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:12
Exact Mass:476.19370504
Heavy Atom Count:33
Complexity:680

Purity/Quality:

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

N-[(R)-[[(1R)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy]methyl]phenoxyphosphinyl]-L-alanine1-MethylethylEster ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC(C)OC(=O)C(C)NP(=O)(COC(C)CN1C=NC2=C(N=CN=C21)N)OC3=CC=CC=C3
Isomeric SMILES:C[C@H](CN1C=NC2=C(N=CN=C21)N)OC[P@](=O)(N[C@@H](C)C(=O)OC(C)C)OC3=CC=CC=C3
Recent ClinicalTrials:A Phase 1b Study Assessing GS-7340 in Treatment-Naive Adults With Chronic Hepatitis B
Recent EU Clinical Trials:A Phase 2a, Open-Label Study to Evaluate the Safety and Efficacy of Selgantolimod (SLGN)-Containing Combination Therapies for the Treatment of Chronic Hepatitis B (CHB)
Uses (S)-Isopropyl 2-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)amino)propanoate is an isomer of Tenofovir Alafenamide (T018555), is a prodrug of Tenofovir (T018500).

Technology Process of N-((R)-(((1R)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy)methyl)phenoxyphosphinyl)-L-alanine 1-methylethyl ester

There total 9 articles about N-((R)-(((1R)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy)methyl)phenoxyphosphinyl)-L-alanine 1-methylethyl ester 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: 81.0%

: 9-[(R)-2-[[(R)-[[(S)-1-(isopropoxycarbonyl)ethyl]amino](phenoxy)phosphinyl]methoxy]propyl]adenine L-tartrate

: 383365-04-6,2053424-88-5,379270-36-7
N-[(R)-[[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl]phenoxyphosphonyl]-L-alanine-1-methylethyl ester

Guidance literature:: With ammonium hydroxide; In dichloromethane; water; pH=8 - 9;

Reference yield:

: 39825-33-7
isopropyl L-alanine

: 379270-35-6
((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphoric acid monophenyl ester

: 379270-37-8,2053424-88-5,379270-36-7
(S)-isopropyl-2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)amino)propanoate

: 383365-04-6,2053424-88-5,379270-36-7
N-[(R)-[[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl]phenoxyphosphonyl]-L-alanine-1-methylethyl ester

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 75 - 80 ℃;

isopropyl L-alanine; In dichloromethane; at -18 ℃; for 1h;
DOI:10.1081/NCN-100002338

Reference yield:

: 147127-20-6
tenofovir

: 108-95-2,27073-41-2
phenol

: 379270-37-8,2053424-88-5,379270-36-7
(S)-isopropyl-2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)amino)propanoate

: 383365-04-6,2053424-88-5,379270-36-7
N-[(R)-[[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl]phenoxyphosphonyl]-L-alanine-1-methylethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide / 16 h / 60 - 100 °C / Large scale

2.1: thionyl chloride / acetonitrile / 2 h / 75 - 85 °C / Large scale

2.2: 3 h / -25 - 35 °C / Large scale

With thionyl chloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In acetonitrile;