{(S)-5-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pent-3-enyl]-2-isopropyl-5-methyl-cyclopent-1-enyl}-propynoic acid methyl 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 methyl ester
• CAS No.: 849104-14-9
• Molecular Formula: C₃₅H₄₆O₃Si
• Molecular Weight: 542.834

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

Chemical Property:

Purity/Quality:

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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 methyl 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 methyl 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 methyl ester (849104-14-9)

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-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 methyl ester (849104-14-9)

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

Reference yield:

(R)-2-tert-butoxymethylene-5-methyl-5-(2-propenyl)cyclopentanone (685901-94-4) → {(S)-5-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pent-3-enyl]-2-isopropyl-5-methyl-cyclopent-1-enyl}-propynoic acid methyl ester (849104-14-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 85 percent / diethyl ether / -20 - 20 °C

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

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

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

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

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

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

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

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

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

9.1: K₂CO₃ / methanol / 1 h / 20 °C

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

10.2: 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; 3.1: Sonogashira coupling / 8.2: Negishi reaction;

DOI:10.1021/ja051547m

upstream raw materials:

methyl 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

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