(Z)-7-[(1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid

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Chemical Name:(Z)-7-[(1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid
CAS No.:913618-03-8
Molecular Formula:C₃₈H₄₈O₅Si
Molecular Weight:612.882
Hs Code.:

Synonyms:(Z)-7-[(1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid

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Chemical Property of (Z)-7-[(1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid

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Technology Process of (Z)-7-[(1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid

There total 12 articles about (Z)-7-[(1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid 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: 76.0%

: 913617-66-0
[5-[2-(tert-butyldiphenylsilanyloxy)ethyl]-2-(4-methoxybenzyloxy)-3-cyclopentenyl]acetaldehyde

: 17814-85-6
(4-carboxybutyl)triphenylphosphonium bromide

: 913618-03-8
(Z)-7-[(1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1016/j.tet.2006.08.068

Reference yield:

: 913617-64-8
(4R)-4-vinyltetrahydropyran-2-one

: 913618-03-8
(Z)-7-[(1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid

Guidance literature:: Multi-step reaction with 9 steps

1.1: dibutylboron trifluoromethane sulfonate; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 °C

1.2: 80 percent / CH₂Cl₂ / 1 h / -78 °C

2.1: camphorsulfonic acid / CH₂Cl₂; cyclohexane / 24 h / 20 °C

3.1: 839.5 mg / LiAlH₄ / diethyl ether / 2 h / 20 °C

4.1: 78 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / toluene / 1.5 h / 50 °C

5.1: 53 percent / imidazole / dimethylformamide / 1 h / 0 °C

6.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

7.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / 20 °C

8.1: 127 mg / p-toluenesulfonic acid / acetone / 1 h / 20 °C

9.1: 76 percent / NaHMDS / tetrahydrofuran / 1 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium hexamethyldisilazane; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone; toluene; 1.1: Mukaiyama aldol reaction / 1.2: Mukaiyama aldol reaction / 7.1: Wittig reaction / 9.1: Wittig reaction;
DOI:10.1016/j.tet.2006.08.068

Reference yield:

: (R)-3-(2-Hydroxy-ethyl)-pent-4-enoic acid

: 913618-03-8
(Z)-7-[(1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid

Guidance literature:: Multi-step reaction with 10 steps

1.1: 1.54 g / camphorsulfonic acid / benzene / 15 h / Heating

2.1: dibutylboron trifluoromethane sulfonate; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 °C

2.2: 80 percent / CH₂Cl₂ / 1 h / -78 °C

3.1: camphorsulfonic acid / CH₂Cl₂; cyclohexane / 24 h / 20 °C

4.1: 839.5 mg / LiAlH₄ / diethyl ether / 2 h / 20 °C

5.1: 78 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / toluene / 1.5 h / 50 °C

6.1: 53 percent / imidazole / dimethylformamide / 1 h / 0 °C

7.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

8.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / 20 °C

9.1: 127 mg / p-toluenesulfonic acid / acetone / 1 h / 20 °C

10.1: 76 percent / NaHMDS / tetrahydrofuran / 1 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium hexamethyldisilazane; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; camphor-10-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone; toluene; benzene; 2.1: Mukaiyama aldol reaction / 2.2: Mukaiyama aldol reaction / 8.1: Wittig reaction / 10.1: Wittig reaction;
DOI:10.1016/j.tet.2006.08.068