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

Base Information

• Chemical Name: ((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate
• CAS No.: 1435752-55-8
• Molecular Formula: C₂₁H₂₀N₆O₇
• Molecular Weight: 468.426
• Mol file: 1435752-55-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about ((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate 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:

(3S,5R)-7-(trimethylsilyl)hept-1-en-6-yne-3,5-diol (1383811-86-6) → ((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate (1435752-55-8)

Guidance literature:

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: 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

With 1H-imidazole; 2,4,6-trimethyl-pyridine; methanol; dmap; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane; formic acid; potassium carbonate; [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc; In tetrahydrofuran; dichloromethane;

Reference yield:

(3S,5R)-5-(tert-butyldimethylsilyloxy)-7-(trimethylsilyl)hept-1-en-6-yn-3-ol (1383811-90-2) → ((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate (1435752-55-8)

Guidance literature:

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: 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

With 2,4,6-trimethyl-pyridine; methanol; dmap; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane; formic acid; potassium carbonate; [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc; In tetrahydrofuran; dichloromethane;

Reference yield:

(1S,3R)-3-(tert-butyldimethylsilyloxy)-1-(oxiran-2-yl)pent-4-yn-1-ol (1383811-98-0) → ((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate (1435752-55-8)

Guidance literature:

Multi-step reaction with 6 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

With 2,4,6-trimethyl-pyridine; methanol; dmap; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane; formic acid; [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; triethylamine; triphenylphosphine; zinc; In tetrahydrofuran; dichloromethane;

upstream raw materials:

(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

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

Downstream raw materials:

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

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