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

Base Information

Chemical Name:((1R,3R,5S)-5-acetoxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclopentyl)methyl 4-nitrobenzoate
CAS No.:1435752-36-5
Molecular Formula:C₂₂H₃₁NO₇Si
Molecular Weight:449.576
Hs Code.:

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

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

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

There total 10 articles about ((1R,3R,5S)-5-acetoxy-3-(tert-butyldimethylsilyloxy)-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: 74.0%

: 1383812-06-3
(1S,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)-3-methylenecyclopentyl acetate

: 122-04-3
4-nitro-benzoyl chloride

: 1435752-36-5
((1R,3R,5S)-5-acetoxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclopentyl)methyl 4-nitrobenzoate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/jo400607v

Reference yield:

: 1383811-86-6
(3S,5R)-7-(trimethylsilyl)hept-1-en-6-yne-3,5-diol

: 1435752-36-5
((1R,3R,5S)-5-acetoxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclopentyl)methyl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 6 steps

1: 1H-imidazole / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere

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

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

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

5: 2,4,6-trimethyl-pyridine; zinc; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

6: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; 2,4,6-trimethyl-pyridine; methanol; dmap; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; dichloromethane;

Reference yield:

: 1383811-90-2
(3S,5R)-5-(tert-butyldimethylsilyloxy)-7-(trimethylsilyl)hept-1-en-6-yn-3-ol

: 1435752-36-5
((1R,3R,5S)-5-acetoxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclopentyl)methyl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 5 steps

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

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere

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

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

5: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With 2,4,6-trimethyl-pyridine; methanol; dmap; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; dichloromethane;