1,3-Cyclopentadiene-1-carboxylic acid, 4-[(3S)-2,2-dimethyl-3-(phenylmethoxy)-4-pentenyl]-2-ethoxy-5-(2-oxo-2 -phenylethylidene)-, ethyl ester, (5E)-

Base Information

Chemical Name:1,3-Cyclopentadiene-1-carboxylic acid, 4-[(3S)-2,2-dimethyl-3-(phenylmethoxy)-4-pentenyl]-2-ethoxy-5-(2-oxo-2 -phenylethylidene)-, ethyl ester, (5E)-
CAS No.:570371-60-7
Molecular Formula:C32H36O5
Molecular Weight:500.635
Hs Code.:

1,3-Cyclopentadiene-1-carboxylic acid,
4-[(3S)-2,2-dimethyl-3-(phenylmethoxy)-4-pentenyl]-2-ethoxy-5-(2-oxo-2
-phenylethylidene)-, ethyl ester, (5E)-

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Chemical Property of 1,3-Cyclopentadiene-1-carboxylic acid, 4-[(3S)-2,2-dimethyl-3-(phenylmethoxy)-4-pentenyl]-2-ethoxy-5-(2-oxo-2 -phenylethylidene)-, ethyl ester, (5E)-

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Technology Process of 1,3-Cyclopentadiene-1-carboxylic acid, 4-[(3S)-2,2-dimethyl-3-(phenylmethoxy)-4-pentenyl]-2-ethoxy-5-(2-oxo-2 -phenylethylidene)-, ethyl ester, (5E)-

There total 10 articles about 1,3-Cyclopentadiene-1-carboxylic acid, 4-[(3S)-2,2-dimethyl-3-(phenylmethoxy)-4-pentenyl]-2-ethoxy-5-(2-oxo-2 -phenylethylidene)-, ethyl ester, (5E)- 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: 56.0%

: 27271-34-7,27271-28-9
(2-ethoxy-3-ethoxycarbonyl-2-propenylidene)triphenylphosphorane

: 570371-55-0
(7S)-7-benzyloxy-6,6-dimethyl-1-phenylnon-8-en-2-yne-1,4-dione

: 570371-57-2
ethyl 4-((3S)-3-benzyloxy-2,2-dimethyl-pent-4-en-1-yl)-2-ethoxy-5(Z)-benzoylmethylidene-1,3-cyclopentadiene-1-carboxylate

: 570371-60-7
ethyl 4-((3S)-3-benzyloxy-2,2-dimethyl-pent-4-en-1-yl)-2-ethoxy-5(E)-benzoylmethylidene-1,3-cyclopentadiene-1-carboxylate

Guidance literature:: In tetrahydrofuran; at 0 ℃; for 24h;
DOI:10.1016/S0040-4020(03)00297-7

Reference yield:

: 147252-93-5
(3S)-3-(benzyloxy)-2,2-dimethyl-4-penten-1-ol

: 570371-60-7
ethyl 4-((3S)-3-benzyloxy-2,2-dimethyl-pent-4-en-1-yl)-2-ethoxy-5(E)-benzoylmethylidene-1,3-cyclopentadiene-1-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 310 mg / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: sec-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

2.2: tetrahydrofuran; hexane / 3 h / 20 °C

2.3: 68 percent / TsOH / H₂O; acetone / 2 h / 0 °C

3.1: 80 percent / tetrahydrofuran / 1 h / 0 °C

4.1: Et₃N / diethyl ether / 12 h / 20 °C

5.1: CuI; (Ph₃P)2PdCl₂; Et₃N / benzene / 15 h / 20 °C

6.1: citric acid / methanol / 0.33 h / 20 °C

7.1: 87 mg / MnO₂ / CH₂Cl₂ / 24 h / 20 °C

8.1: 22 percent / tetrahydrofuran / 24 h / 0 °C

With manganese(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; oxalyl dichloride; sec.-butyllithium; dimethyl sulfoxide; triethylamine; citric acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; benzene; 1.1: Swern oxidation / 2.2: Wittig reaction / 5.1: Sonogashira coupling;
DOI:10.1016/S0040-4020(03)00297-7

Reference yield:

: 20374-33-8
(R)-(+)-3-(Benzyloxy)-4,5-dihydro-4,4-dimethyl-furan-2(3H)-on

: 570371-60-7
ethyl 4-((3S)-3-benzyloxy-2,2-dimethyl-pent-4-en-1-yl)-2-ethoxy-5(E)-benzoylmethylidene-1,3-cyclopentadiene-1-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 484 mg / DIBAL / toluene / 2 h / -78 °C

2.1: BuLi / hexane; tetrahydrofuran

2.2: 323 mg / tetrahydrofuran; hexane / 3 h / 0 °C

3.1: 310 mg / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: sec-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

4.2: tetrahydrofuran; hexane / 3 h / 20 °C

4.3: 68 percent / TsOH / H₂O; acetone / 2 h / 0 °C

5.1: 80 percent / tetrahydrofuran / 1 h / 0 °C

6.1: Et₃N / diethyl ether / 12 h / 20 °C

7.1: CuI; (Ph₃P)2PdCl₂; Et₃N / benzene / 15 h / 20 °C

8.1: citric acid / methanol / 0.33 h / 20 °C

9.1: 87 mg / MnO₂ / CH₂Cl₂ / 24 h / 20 °C

10.1: 22 percent / tetrahydrofuran / 24 h / 0 °C

With manganese(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; oxalyl dichloride; sec.-butyllithium; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; citric acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; benzene; 2.2: Wittig reaction / 3.1: Swern oxidation / 4.2: Wittig reaction / 7.1: Sonogashira coupling;
DOI:10.1016/S0040-4020(03)00297-7