(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

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Chemical Name:(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
CAS No.:658080-33-2
Molecular Formula:C₅₉H₆₆O₄Si
Molecular Weight:867.256
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 12 articles about (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 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:

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

: 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

Guidance literature:: Multi-step reaction with 7 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

With n-butyllithium; formic acid; samarium diiodide; trichloroisocyanuric acid; Dess-Martin periodane; triethylamine; 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

: 658080-33-2
(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

Guidance literature:: Multi-step reaction with 8 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

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

Reference yield:

: (S)-3-Methyl-4-trityloxy-butan-1-ol

: 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

Guidance literature:: Multi-step reaction with 11 steps

1.1: imidazole / dimethylformamide / 1 h / 20 °C

2.1: trifluoroacetic anhydride; trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

2.2: 85 percent / MeOH; NEt₃ / 1.5 h / 0 °C

3.1: PBu₃ / dimethylformamide / 1.5 h / 20 °C

4.1: m-chloroperbenzoic acid; NaHCO₃ / CH₂Cl₂ / 1.5 h / 20 °C

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

5.2: tetrahydrofuran / 1.5 h / -78 °C

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

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

7.1: 67 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

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

8.2: 73 percent / Al₂O₃

9.1: 71 percent / NEt₃ / tetrahydrofuran / 7 h / 20 °C

10.1: 79 percent / trichloroisocyanuric acid / benzene; diethyl ether / 21 h / 0 °C

11.1: 98 percent / Pd(PPh₃)4 / 1-methyl-pyrrolidin-2-one / 22 h / 100 °C

With 1H-imidazole; n-butyllithium; formic acid; samarium diiodide; tributylphosphine; trichloroisocyanuric acid; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; trifluoroacetic anhydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 9.1: Michael addition;
DOI:10.1002/anie.200351750