6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-

Base Information

• Chemical Name: 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-
• CAS No.: 188399-46-4
• Molecular Formula: C12H15N5O3
• Molecular Weight: 277
• Mol file: 188399-46-4.mol

Synonyms:6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-;2-Amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one;[1R-(1α,3α,4β)]-2-AMino-1,9-dihydro-9-[4-hydroxy-3-(hydroxyMethyl)-2-Methylenecyclopentyl]-6H-purin-6-one;ent-Entecavir

Chemical Property of 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-

Chemical Property:

• PKA: 9?+-.0.20(Predicted)
• PSA: 130.05000
• Density: 1.81
• LogP: -0.24660
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

ent-Entecavir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: ent-Entecavir is an enantiomeric impurity of the antiviral drug Entecavir (E558900).

Technology Process of 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-

There total 16 articles about 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]- 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: 60.0%

((1 R,3S,5S)-5-acetoxy-3-(2-amino-6-chloro-9H-purin-9-yl)-2-methylenecyclopentyl)methyl acetate (1383812-22-3) → 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one (142217-69-4,1333204-94-6,188399-46-4)

Guidance literature:

((1 R,3S,5S)-5-acetoxy-3-(2-amino-6-chloro-9H-purin-9-yl)-2-methylenecyclopentyl)methyl acetate; With sodium hydroxide; at 80 ℃; for 2h;

With hydrogenchloride; In water; at 0 ℃; pH=7;

Reference yield:

((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate (1435752-55-8) → 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one (142217-69-4,1333204-94-6,188399-46-4)

Guidance literature:

((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate; With sodium methylate; In methanol; at 20 ℃; for 0.5h; Inert atmosphere;

With hydrogenchloride; tert-butyl methyl ether; In methanol; pH=7; Inert atmosphere;

Reference yield:

(3S,5R)-7-(trimethylsilyl)hept-1-en-6-yne-3,5-diol (1383811-86-6) → 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one (142217-69-4,1333204-94-6,188399-46-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 1H-imidazole / tetrahydrofuran / 0 - 15 °C / Inert atmosphere

2.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere

4.1: chloro-trimethyl-silane; 2,4,6-trimethyl-pyridine; zinc / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

5.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

6.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

7.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere

8.1: sodium hydroxide / 2 h / 80 °C

8.2: 0 °C / pH 7

With pyridine; 1H-imidazole; 2,4,6-trimethyl-pyridine; methanol; dmap; chloro-trimethyl-silane; di-isopropyl azodicarboxylate; hydrogen fluoride; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium hydroxide; zinc; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(1S,3R)-3-(tert-butyldimethylsilyloxy)-1-(oxiran-2-yl)pent-4-yn-1-ol

(3S,5R)-7-(trimethylsilyl)hept-1-en-6-yne-3,5-diol

(3S,5R)-5-(tert-butyldimethylsilyloxy)-7-(trimethylsilyl)hept-1-en-6-yn-3-ol

(3S,5R)-5-(tert-butyldimethylsilyloxy)hept-1-en-6-yn-3-ol