(S)-3-[(S)-2-((1E,6E)-(3S,5S)-3-Benzyloxy-7-iodo-5-methyl-hepta-1,6-dienyl)-3-methyl-5-oxo-cyclopent-1-enyl]-butyraldehyde

Base Information

Chemical Name:(S)-3-[(S)-2-((1E,6E)-(3S,5S)-3-Benzyloxy-7-iodo-5-methyl-hepta-1,6-dienyl)-3-methyl-5-oxo-cyclopent-1-enyl]-butyraldehyde
CAS No.:658080-35-4
Molecular Formula:C₂₅H₃₁IO₃
Molecular Weight:506.424
Hs Code.:

Synonyms:(S)-3-[(S)-2-((1E,6E)-(3S,5S)-3-Benzyloxy-7-iodo-5-methyl-hepta-1,6-dienyl)-3-methyl-5-oxo-cyclopent-1-enyl]-butyraldehyde

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Chemical Property of (S)-3-[(S)-2-((1E,6E)-(3S,5S)-3-Benzyloxy-7-iodo-5-methyl-hepta-1,6-dienyl)-3-methyl-5-oxo-cyclopent-1-enyl]-butyraldehyde

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Technology Process of (S)-3-[(S)-2-((1E,6E)-(3S,5S)-3-Benzyloxy-7-iodo-5-methyl-hepta-1,6-dienyl)-3-methyl-5-oxo-cyclopent-1-enyl]-butyraldehyde

There total 18 articles about (S)-3-[(S)-2-((1E,6E)-(3S,5S)-3-Benzyloxy-7-iodo-5-methyl-hepta-1,6-dienyl)-3-methyl-5-oxo-cyclopent-1-enyl]-butyraldehyde 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: 86.0%

: 658080-42-3
(S)-3-((1E,6E)-(3S,5S)-3-Benzyloxy-7-iodo-5-methyl-hepta-1,6-dienyl)-2-((S)-3-hydroxy-1-methyl-propyl)-4-methyl-cyclopent-2-enone

: 658080-35-4
(S)-3-[(S)-2-((1E,6E)-(3S,5S)-3-Benzyloxy-7-iodo-5-methyl-hepta-1,6-dienyl)-3-methyl-5-oxo-cyclopent-1-enyl]-butyraldehyde

Guidance literature:: With dipyridinium dichromate; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1002/anie.200351750

Reference yield:

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

: 658080-35-4
(S)-3-[(S)-2-((1E,6E)-(3S,5S)-3-Benzyloxy-7-iodo-5-methyl-hepta-1,6-dienyl)-3-methyl-5-oxo-cyclopent-1-enyl]-butyraldehyde

Guidance literature:: Multi-step reaction with 12 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

9.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

10.1: 90 percent / CrCl₂ / tetrahydrofuran / 0.67 h / 20 °C

11.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 6 h / 20 °C

12.1: 86 percent / pyridinium dichromate / CH₂Cl₂ / 1 h / 20 °C

With chromium dichloride; dipyridinium dichromate; n-butyllithium; formic acid; samarium diiodide; trichloroisocyanuric acid; tetrabutyl ammonium fluoride; 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 / 10.1: Takai reaction;
DOI:10.1002/anie.200351750

Reference yield:

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

: 658080-35-4
(S)-3-[(S)-2-((1E,6E)-(3S,5S)-3-Benzyloxy-7-iodo-5-methyl-hepta-1,6-dienyl)-3-methyl-5-oxo-cyclopent-1-enyl]-butyraldehyde

Guidance literature:: Multi-step reaction with 13 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

10.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

11.1: 90 percent / CrCl₂ / tetrahydrofuran / 0.67 h / 20 °C

12.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 6 h / 20 °C

13.1: 86 percent / pyridinium dichromate / CH₂Cl₂ / 1 h / 20 °C

With chromium dichloride; dipyridinium dichromate; n-butyllithium; formic acid; samarium diiodide; trichloroisocyanuric acid; tetrabutyl ammonium fluoride; 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 / 11.1: Takai reaction;
DOI:10.1002/anie.200351750