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142217-69-4

Basic Information
CAS No.: 142217-69-4
Name: Entecavir
Molecular Structure:
Molecular Structure of 142217-69-4 (Entecavir)
Formula: C12H15N5O3
Molecular Weight: 277.28
Synonyms: 2-amino-9-[(3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidene-cyclopentyl]-3H-purin-6-one;ETV;6H-Purin-6-one, 2-amino-1,9-dihydro-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-;2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidene-cyclopentyl]-3H-purin-6-one;SQ 34676;BMS 200475;Baraclude;6H-Purin-6-one,2-amino-1,9-dihydro-9- [(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2- methylenecyclopentyl]-;Taizhou hikong chemical sell Entecavir;Entecavi;Enteca;Entecavir(monohydrate)--Crude Product;
EINECS: 604-279-5
Density: 1.81 g/cm3
Melting Point: 249-252 °C
Boiling Point: 734.2 °C at 760 mmHg
Flash Point: 397.9 °C
Solubility:
Appearance: white to off-white/yellow crystalline powder
Hazard Symbols:
Risk Codes:
Safety: 24/25
Transport Information:
PSA: 130.05000
LogP: -0.24660
Synthetic route
1383812-22-3

((1 R,3S,5S)-5-acetoxy-3-(2-amino-6-chloro-9H-purin-9-yl)-2-methylenecyclopentyl)methyl acetate

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Stage #1: ((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;
Stage #2: With hydrogenchloride In water at 0℃; pH=7;
60%
1383811-98-0

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

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: chloro-trimethyl-silane; 2,4,6-trimethyl-pyridine; zinc / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
2.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
3.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
4.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
5.1: sodium hydroxide / 2 h / 80 °C
5.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 6 steps
1.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
2.1: manganese; 2,4,6-collidine hydrochloride / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 4 h / 20 °C
3.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
4.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
5.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
6.1: sodium hydroxide / 2 h / 80 °C
6.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 7 steps
1.1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
2.1: 2,4,6-trimethyl-pyridine; zinc; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
3.1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
4.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; methanol / 4 h / 0 - 20 °C / Inert atmosphere; Enzymatic reaction
5.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
5.2: 4.17 h / -10 °C / Inert atmosphere
6.1: formic acid / 9 h / 50 °C / Inert atmosphere
7.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
7.2: pH 7 / Inert atmosphere
View Scheme
1383811-86-6

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

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
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
View Scheme
Multi-step reaction with 8 steps
1.1: 1H-imidazole / tetrahydrofuran / 5 h / 0 - 20 °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
View Scheme
Multi-step reaction with 9 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: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
5.1: manganese; 2,4,6-collidine hydrochloride / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 4 h / 20 °C
6.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
7.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
8.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
9.1: sodium hydroxide / 2 h / 80 °C
9.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 9 steps
1.1: 1H-imidazole / tetrahydrofuran / 5 h / 0 - 20 °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: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
5.1: manganese; 2,4,6-collidine hydrochloride / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 4 h / 20 °C
6.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
7.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
8.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
9.1: sodium hydroxide / 2 h / 80 °C
9.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 10 steps
1.1: 1H-imidazole / tetrahydrofuran / 5 h / 0 - 20 °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: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
5.1: 2,4,6-trimethyl-pyridine; zinc; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
6.1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
7.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; methanol / 4 h / 0 - 20 °C / Inert atmosphere; Enzymatic reaction
8.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
8.2: 4.17 h / -10 °C / Inert atmosphere
9.1: formic acid / 9 h / 50 °C / Inert atmosphere
10.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
10.2: pH 7 / Inert atmosphere
View Scheme
1383811-90-2

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

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
3.1: chloro-trimethyl-silane; 2,4,6-trimethyl-pyridine; zinc / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
4.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
5.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
6.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
7.1: sodium hydroxide / 2 h / 80 °C
7.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 8 steps
1.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
3.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
4.1: manganese; 2,4,6-collidine hydrochloride / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 4 h / 20 °C
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
View Scheme
Multi-step reaction with 9 steps
1.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
3.1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
4.1: 2,4,6-trimethyl-pyridine; zinc; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
5.1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
6.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; methanol / 4 h / 0 - 20 °C / Inert atmosphere; Enzymatic reaction
7.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
7.2: 4.17 h / -10 °C / Inert atmosphere
8.1: formic acid / 9 h / 50 °C / Inert atmosphere
9.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
9.2: pH 7 / Inert atmosphere
View Scheme
1383811-94-6

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

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
2.1: chloro-trimethyl-silane; 2,4,6-trimethyl-pyridine; zinc / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
3.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
4.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
5.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
6.1: sodium hydroxide / 2 h / 80 °C
6.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 7 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
2.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
3.1: manganese; 2,4,6-collidine hydrochloride / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 4 h / 20 °C
4.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
5.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
6.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
7.1: sodium hydroxide / 2 h / 80 °C
7.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 8 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
2.1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
3.1: 2,4,6-trimethyl-pyridine; zinc; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
4.1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
5.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; methanol / 4 h / 0 - 20 °C / Inert atmosphere; Enzymatic reaction
6.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
6.2: 4.17 h / -10 °C / Inert atmosphere
7.1: formic acid / 9 h / 50 °C / Inert atmosphere
8.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
8.2: pH 7 / Inert atmosphere
View Scheme
1383812-02-9

(1S,3R)-3-(tert-butyldimethylsilyloxy)-1-(oxiran-2-yl)pent-4-ynyl acetate

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: manganese; 2,4,6-collidine hydrochloride / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 4 h / 20 °C
2.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
3.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
4.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
5.1: sodium hydroxide / 2 h / 80 °C
5.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 6 steps
1.1: 2,4,6-trimethyl-pyridine; zinc; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
2.1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
3.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; methanol / 4 h / 0 - 20 °C / Inert atmosphere; Enzymatic reaction
4.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
4.2: 4.17 h / -10 °C / Inert atmosphere
5.1: formic acid / 9 h / 50 °C / Inert atmosphere
6.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
6.2: pH 7 / Inert atmosphere
View Scheme
1383812-06-3

(1S,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)-3-methylenecyclopentyl acetate

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
2.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
3.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
4.1: sodium hydroxide / 2 h / 80 °C
4.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 5 steps
1.1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; methanol / 4 h / 0 - 20 °C / Inert atmosphere; Enzymatic reaction
3.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
3.2: 4.17 h / -10 °C / Inert atmosphere
4.1: formic acid / 9 h / 50 °C / Inert atmosphere
5.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
5.2: pH 7 / Inert atmosphere
View Scheme
701278-65-1

(1S,2R,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)-3-methylenecyclopentanol

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
2.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
3.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
4.1: sodium hydroxide / 2 h / 80 °C
4.2: 0 °C / pH 7
View Scheme
1383812-10-9

((1R,3R,5S)-5-acetoxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclopentyl)methyl acetate

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
2.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
3.1: sodium hydroxide / 2 h / 80 °C
3.2: 0 °C / pH 7
View Scheme

((1R,3R,5S)-5-acetoxy-3-hydroxy-2-methylenecyclo-pentyl) methyl acetate

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
2.1: sodium hydroxide / 2 h / 80 °C
2.2: 0 °C / pH 7
View Scheme
1435752-36-5

((1R,3R,5S)-5-acetoxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclopentyl)methyl 4-nitrobenzoate

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; methanol / 4 h / 0 - 20 °C / Inert atmosphere; Enzymatic reaction
2.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
2.2: 4.17 h / -10 °C / Inert atmosphere
3.1: formic acid / 9 h / 50 °C / Inert atmosphere
4.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
4.2: pH 7 / Inert atmosphere
View Scheme
1435752-42-3

((1R,3R,5S)-5-acetoxy-3-hydroxy-2-methylenecyclopentyl)methyl 4-nitrobenzoate

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
1.2: 4.17 h / -10 °C / Inert atmosphere
2.1: formic acid / 9 h / 50 °C / Inert atmosphere
3.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
3.2: pH 7 / Inert atmosphere
View Scheme
1435752-48-9

((1R,3S,5S)-5-acetoxy-3-(2-amino-6-chloro-9H-purin-9-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: formic acid / 9 h / 50 °C / Inert atmosphere
2.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
2.2: pH 7 / Inert atmosphere
View Scheme
10310-21-1

2-Amino-6-chloropurin

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
1.2: 4.17 h / -10 °C / Inert atmosphere
2.1: formic acid / 9 h / 50 °C / Inert atmosphere
3.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
3.2: pH 7 / Inert atmosphere
View Scheme
1435752-55-8

((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Stage #1: ((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;
Stage #2: With hydrogenchloride; tert-butyl methyl ether In methanol pH=7; Inert atmosphere;
2.37 g

C10H20O2Si

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: sodium acetate; dihydrogen peroxide / tetrahydrofuran; water / 0.83 h / 0 - 20 °C / Inert atmosphere
1.2: Enzymatic reaction
2.1: 1H-imidazole / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere
3.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
5.1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
6.1: 2,4,6-trimethyl-pyridine; zinc; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
7.1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
8.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; methanol / 4 h / 0 - 20 °C / Inert atmosphere; Enzymatic reaction
9.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
9.2: 4.17 h / -10 °C / Inert atmosphere
10.1: formic acid / 9 h / 50 °C / Inert atmosphere
11.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
11.2: pH 7 / Inert atmosphere
View Scheme
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

1795-62-6

ω-chlorocaprylic acid

N-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-hydroxymethyl-2-methylene-cyclopentyl]-2-6H-purin-6-oneoctanamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 30℃; for 8h;74%
112-16-3

n-dodecanoyl chloride

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

N-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-hydroxymethyl-2-methylene-cyclopentyl]-2-6H-purin-6-onelaurylamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 50℃; for 8h;68%
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Reaxys ID: 30033682

Reaxys ID: 30033682

Reaxys ID: 30033679

Reaxys ID: 30033679

142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(((S)-1-isopropoxycarbonylethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 20 °C
2: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C
View Scheme
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(((S)-1-cyclohexyloxycarbonylethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 20 °C
2: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C
View Scheme
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-((methoxycarbonylmethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 20 °C
2: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C
View Scheme
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-((ethoxycarbonylmethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 20 °C
2: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C
View Scheme
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-((isopropoxycarbonylmethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 20 °C
2: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C
View Scheme
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(((S)-1-ethoxycarbonylethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 20 °C
2: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C
View Scheme
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

A

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(((R)-(1S)-1-ethoxycarbonylethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

B

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(((S)-(1S)-1-ethoxycarbonylethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N,N-dimethyl-formamide / 20 °C
2: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C
3: Diacel's Chiralpak AS / acetonitrile; ethanol
View Scheme
Multi-step reaction with 3 steps
1: N,N-dimethyl-formamide / 20 °C
2: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C
3: Diacel's Chiralpak AS / acetonitrile; isopropyl alcohol
View Scheme
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

4637-24-5

N,N-dimethyl-formamide dimethyl acetal

C15H20N6O3

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃;
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  • Entecavir/ Entecavir powder CAS Number:142217-69-4

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    142217-69-4

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  • CAS NO.:142217-69-4 Entecavir   C12H15N5O3

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    CAS NO.:142217-69-4 Entecavir C12H15N5O3

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    142217-69-4

    Top Purity CAS 142217-69-4 with fast shipping

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Specification

1. Introduction of Entecavir

Entecavir, with the IUPAC Name of 2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one, is one kind of white to off-white or yellow crystalline powder. This belongs to the product categories which include Antiviral Agents; Nucleotides and Nucleosides; Bases & Related Reagents; Intermediates & Fine Chemicals; Nucleotides; Pharmaceuticals.

2. Properties of Entecavir

Entecavir has the following property datas: (1)Freely Rotating Bonds: 4; (2)Polar Surface Area: 125.76 ?2; (3)Flash Point: 397.9 °C; (4)Enthalpy of Vaporization: 112.46 kJ/mol; (5)Boiling Point: 734.2 °C at 760 mmHg; (6)Vapour Pressure: 1.24E-22 mmHg at 25°C; (7)Melting Point: 249-252°C.

3. Structure Descriptors of Entecavir

You could convert the following datas into the molecular structure:
(1).SMILES: O.C=C3[C@H](CO)[C@@H](O)C[C@@H]3n2cnc1c2\N=C(\N)NC1=O Copy
(2).InChI: InChI=1/C12H15N5O3.H2O/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20;/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20);1H2/t6-,7-,8-;/m0./s1 Copy
(3).InChIKey: YXPVEXCTPGULBZ-WQYNNSOEBH
(4).Std. InChI: InChI=1S/C12H15N5O3.H2O/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20;/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20);1H2/t6-,7-,8-;/m0./s1 Copy
(5).Std. InChIKey: YXPVEXCTPGULBZ-WQYNNSOESA-N

4. Use of Entecavir

Entecavir is used to treat chronic hepatitis B. And it also helps prevent the hepatitis B virus from multiplying and infecting new liver cells. Besides, Entecavir is also indicated for the treatment of chronic hepatitis B in adults with HIV/AIDS infection, but Entecavir is not active against HIV.