{(S)-5-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pent-3-enyl]-2-isopropyl-5-methyl-cyclopent-1-enyl}-propynoic acid isopropyl ester

Base Information

• Chemical Name: {(S)-5-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pent-3-enyl]-2-isopropyl-5-methyl-cyclopent-1-enyl}-propynoic acid isopropyl ester
• CAS No.: 868562-47-4
• Molecular Formula: C₃₇H₅₀O₃Si
• Molecular Weight: 570.888
• Mol file: 868562-47-4.mol

Synonyms:{(S)-5-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pent-3-enyl]-2-isopropyl-5-methyl-cyclopent-1-enyl}-propynoic acid isopropyl ester

Chemical Property of {(S)-5-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pent-3-enyl]-2-isopropyl-5-methyl-cyclopent-1-enyl}-propynoic acid isopropyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(S)-5-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pent-3-enyl]-2-isopropyl-5-methyl-cyclopent-1-enyl}-propynoic acid isopropyl ester

There total 11 articles about {(S)-5-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pent-3-enyl]-2-isopropyl-5-methyl-cyclopent-1-enyl}-propynoic acid isopropyl ester 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:

2-tert-butoxymethylene-5-methyl-cyclopentanone (836628-64-9) → {(S)-5-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pent-3-enyl]-2-isopropyl-5-methyl-cyclopent-1-enyl}-propynoic acid isopropyl ester (868562-47-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: LDA / 1,2-dimethoxy-ethane / -78 - 0 °C

1.2: trimethyltin chloride / 1,2-dimethoxy-ethane; 2-methyl-propan-2-ol / 0.08 h / 0 °C

1.3: [(η³-C3H5)PdCl]2; (S,S)-1,2-[(o-PPh2C6H4)C(O)NH]2-cyclohexyl / 1,2-dimethoxy-ethane / -78 - 20 °C

2.1: 85 percent / diethyl ether / -20 - 20 °C

3.1: LDA / tetrahydrofuran; hexane / -78 - 0 °C

3.2: tetrahydrofuran; hexane / 2 h / 20 °C

4.1: Pd₂(dba)3*CHCl₃; PPh₃; CuI / n-butylamime / benzene / 18 h / 50 °C

5.1: NMO; aq. OsO₄ / CH₂Cl₂ / 8 h / 20 °C

6.1: aq. NaIO₄ / acetone / 1 h / 20 °C

7.1: NaBH₄ / methanol / 0.17 h / 20 °C

8.1: I₂; PPh₃; imidazole / acetonitrile; diethyl ether / 2 h / 20 °C

9.1: ZnCl₂; t-BuLi / tetrahydrofuran; pentane / 1.08 h / -78 - 20 °C

9.2: Pd(PPh₃)4 / tetrahydrofuran; pentane / 20 °C

10.1: K₂CO₃ / methanol / 1 h / 20 °C

11.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

11.2: tetrahydrofuran; hexane / -78 - 20 °C

With 1H-imidazole; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; iodine; tert.-butyl lithium; potassium carbonate; triphenylphosphine; zinc(II) chloride; lithium diisopropyl amide; N-butylamine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; acetone; acetonitrile; pentane; benzene; 4.1: Sonogashira coupling / 9.2: Negishi reaction;

DOI:10.1021/ja051547m

Reference yield:

(R)-5-isopropyl-2-methyl-2-(2-propenyl)cyclopentanone (849103-97-5) → {(S)-5-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pent-3-enyl]-2-isopropyl-5-methyl-cyclopent-1-enyl}-propynoic acid isopropyl ester (868562-47-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: LDA / tetrahydrofuran; hexane / -78 - 0 °C

1.2: tetrahydrofuran; hexane / 2 h / 20 °C

2.1: Pd₂(dba)3*CHCl₃; PPh₃; CuI / n-butylamime / benzene / 18 h / 50 °C

3.1: NMO; aq. OsO₄ / CH₂Cl₂ / 8 h / 20 °C

4.1: aq. NaIO₄ / acetone / 1 h / 20 °C

5.1: NaBH₄ / methanol / 0.17 h / 20 °C

6.1: I₂; PPh₃; imidazole / acetonitrile; diethyl ether / 2 h / 20 °C

7.1: ZnCl₂; t-BuLi / tetrahydrofuran; pentane / 1.08 h / -78 - 20 °C

7.2: Pd(PPh₃)4 / tetrahydrofuran; pentane / 20 °C

8.1: K₂CO₃ / methanol / 1 h / 20 °C

9.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

9.2: tetrahydrofuran; hexane / -78 - 20 °C

With 1H-imidazole; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; iodine; tert.-butyl lithium; potassium carbonate; triphenylphosphine; zinc(II) chloride; lithium diisopropyl amide; N-butylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; acetonitrile; pentane; benzene; 2.1: Sonogashira coupling / 7.2: Negishi reaction;

DOI:10.1021/ja051547m

Reference yield:

(R)-5-allyl-2-isopropyl-5-methyl-1-trifluoromethanesulfonyloxycyclopentene (849103-98-6) → {(S)-5-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pent-3-enyl]-2-isopropyl-5-methyl-cyclopent-1-enyl}-propynoic acid isopropyl ester (868562-47-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Pd₂(dba)3*CHCl₃; PPh₃; CuI / n-butylamime / benzene / 18 h / 50 °C

2.1: NMO; aq. OsO₄ / CH₂Cl₂ / 8 h / 20 °C

3.1: aq. NaIO₄ / acetone / 1 h / 20 °C

4.1: NaBH₄ / methanol / 0.17 h / 20 °C

5.1: I₂; PPh₃; imidazole / acetonitrile; diethyl ether / 2 h / 20 °C

6.1: ZnCl₂; t-BuLi / tetrahydrofuran; pentane / 1.08 h / -78 - 20 °C

6.2: Pd(PPh₃)4 / tetrahydrofuran; pentane / 20 °C

7.1: K₂CO₃ / methanol / 1 h / 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: tetrahydrofuran; hexane / -78 - 20 °C

With 1H-imidazole; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; iodine; tert.-butyl lithium; potassium carbonate; triphenylphosphine; zinc(II) chloride; N-butylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; acetonitrile; pentane; benzene; 1.1: Sonogashira coupling / 6.2: Negishi reaction;

DOI:10.1021/ja051547m

upstream raw materials:

isopropyl chloroformate

(E,R)-5-(2-ethynyl-3-isopropyl-1-methylcyclopent-2-enyl)-3-methylpent-2-en-1-ol tert-butyldiphenyl ether

3-((R)-3-Isopropyl-1-methyl-2-trimethylsilanylethynyl-cyclopent-2-enyl)-propane-1,2-diol

2-tert-butoxymethylene-5-methyl-cyclopentanone