(S)-3-((E)-(3S,5S)-3-Benzyloxy-6-hydroxy-5-methyl-hex-1-enyl)-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-4-methyl-cyclopent-2-enone

Base Information

Chemical Name:(S)-3-((E)-(3S,5S)-3-Benzyloxy-6-hydroxy-5-methyl-hex-1-enyl)-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-4-methyl-cyclopent-2-enone
CAS No.:658080-40-1
Molecular Formula:C₄₀H₅₂O₄Si
Molecular Weight:624.936
Hs Code.:

Synonyms:(S)-3-((E)-(3S,5S)-3-Benzyloxy-6-hydroxy-5-methyl-hex-1-enyl)-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-4-methyl-cyclopent-2-enone

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Chemical Property of (S)-3-((E)-(3S,5S)-3-Benzyloxy-6-hydroxy-5-methyl-hex-1-enyl)-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-4-methyl-cyclopent-2-enone

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Technology Process of (S)-3-((E)-(3S,5S)-3-Benzyloxy-6-hydroxy-5-methyl-hex-1-enyl)-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-4-methyl-cyclopent-2-enone

There total 14 articles about (S)-3-((E)-(3S,5S)-3-Benzyloxy-6-hydroxy-5-methyl-hex-1-enyl)-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-4-methyl-cyclopent-2-enone 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: 94.0%

: 658080-33-2
(S)-3-((E)-(3S,5S)-3-Benzyloxy-5-methyl-6-trityloxy-hex-1-enyl)-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-4-methyl-cyclopent-2-enone

: 658080-40-1
(S)-3-((E)-(3S,5S)-3-Benzyloxy-6-hydroxy-5-methyl-hex-1-enyl)-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-4-methyl-cyclopent-2-enone

Guidance literature:: With zinc dibromide; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1002/anie.200351750

Reference yield:

: 658080-23-0
(S)-3-methyl-4-(trityloxy)butanal

: 658080-40-1
(S)-3-((E)-(3S,5S)-3-Benzyloxy-6-hydroxy-5-methyl-hex-1-enyl)-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-4-methyl-cyclopent-2-enone

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

1.2: tetrahydrofuran / 1.5 h / -78 °C

2.1: HCOOH / diethyl ether / 5.5 h / 20 °C

2.2: NH₃ / H₂O; methanol / 1.5 h / 20 °C

3.1: 67 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

4.1: SmI₂ / tetrahydrofuran / 1 h / 20 °C

4.2: 73 percent / Al₂O₃

5.1: 71 percent / NEt₃ / tetrahydrofuran / 7 h / 20 °C

6.1: 79 percent / trichloroisocyanuric acid / benzene; diethyl ether / 21 h / 0 °C

7.1: 98 percent / Pd(PPh₃)4 / 1-methyl-pyrrolidin-2-one / 22 h / 100 °C

8.1: 94 percent / ZnBr₂ / CH₂Cl₂ / 1.5 h / 20 °C

With n-butyllithium; formic acid; samarium diiodide; trichloroisocyanuric acid; Dess-Martin periodane; triethylamine; zinc dibromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; dichloromethane; benzene; 5.1: Michael addition;
DOI:10.1002/anie.200351750

Reference yield:

: (S)-3-Methyl-4-trityloxy-butyronitrile

: 658080-40-1
(S)-3-((E)-(3S,5S)-3-Benzyloxy-6-hydroxy-5-methyl-hex-1-enyl)-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-4-methyl-cyclopent-2-enone

Guidance literature:: Multi-step reaction with 9 steps

1.1: diisobutyl aluminium hydride / CH₂Cl₂ / 0.5 h / -78 °C

2.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

2.2: tetrahydrofuran / 1.5 h / -78 °C

3.1: HCOOH / diethyl ether / 5.5 h / 20 °C

3.2: NH₃ / H₂O; methanol / 1.5 h / 20 °C

4.1: 67 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

5.1: SmI₂ / tetrahydrofuran / 1 h / 20 °C

5.2: 73 percent / Al₂O₃

6.1: 71 percent / NEt₃ / tetrahydrofuran / 7 h / 20 °C

7.1: 79 percent / trichloroisocyanuric acid / benzene; diethyl ether / 21 h / 0 °C

8.1: 98 percent / Pd(PPh₃)4 / 1-methyl-pyrrolidin-2-one / 22 h / 100 °C

9.1: 94 percent / ZnBr₂ / CH₂Cl₂ / 1.5 h / 20 °C

With n-butyllithium; formic acid; samarium diiodide; trichloroisocyanuric acid; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; zinc dibromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; dichloromethane; benzene; 6.1: Michael addition;
DOI:10.1002/anie.200351750