(4E,9E)-(3S,6S,8S,11S,13S)-6-Benzyloxy-11-hydroxy-3,8,13-trimethyl-2,3,6,7,8,11,12,13-octahydro-cyclopentacyclododecen-1-one

Base Information

Chemical Name:(4E,9E)-(3S,6S,8S,11S,13S)-6-Benzyloxy-11-hydroxy-3,8,13-trimethyl-2,3,6,7,8,11,12,13-octahydro-cyclopentacyclododecen-1-one
CAS No.:658080-36-5
Molecular Formula:C₂₅H₃₂O₃
Molecular Weight:380.527
Hs Code.:

Synonyms:(4E,9E)-(3S,6S,8S,11S,13S)-6-Benzyloxy-11-hydroxy-3,8,13-trimethyl-2,3,6,7,8,11,12,13-octahydro-cyclopentacyclododecen-1-one

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Chemical Property of (4E,9E)-(3S,6S,8S,11S,13S)-6-Benzyloxy-11-hydroxy-3,8,13-trimethyl-2,3,6,7,8,11,12,13-octahydro-cyclopentacyclododecen-1-one

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Technology Process of (4E,9E)-(3S,6S,8S,11S,13S)-6-Benzyloxy-11-hydroxy-3,8,13-trimethyl-2,3,6,7,8,11,12,13-octahydro-cyclopentacyclododecen-1-one

There total 19 articles about (4E,9E)-(3S,6S,8S,11S,13S)-6-Benzyloxy-11-hydroxy-3,8,13-trimethyl-2,3,6,7,8,11,12,13-octahydro-cyclopentacyclododecen-1-one 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: 62.0%

: 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

: 658080-36-5
(4E,9E)-(3S,6S,8S,11S,13S)-6-Benzyloxy-11-hydroxy-3,8,13-trimethyl-2,3,6,7,8,11,12,13-octahydro-cyclopentacyclododecen-1-one

: 658080-43-4
(4E,9E)-(3S,6S,8S,11R,13S)-6-Benzyloxy-11-hydroxy-3,8,13-trimethyl-2,3,6,7,8,11,12,13-octahydro-cyclopentacyclododecen-1-one

Guidance literature:: With chromium dichloride; nickel dichloride; In dimethyl sulfoxide; at 50 ℃; for 24h;
DOI:10.1002/anie.200351750

Reference yield:

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

: 658080-36-5
(4E,9E)-(3S,6S,8S,11S,13S)-6-Benzyloxy-11-hydroxy-3,8,13-trimethyl-2,3,6,7,8,11,12,13-octahydro-cyclopentacyclododecen-1-one

Guidance literature:: Multi-step reaction with 13 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

13.1: 14 percent / CrCl₂; NiCl₂ / dimethylsulfoxide / 24 h / 50 °C

With chromium dichloride; dipyridinium dichromate; n-butyllithium; formic acid; samarium diiodide; trichloroisocyanuric acid; tetrabutyl ammonium fluoride; Dess-Martin periodane; triethylamine; nickel dichloride; zinc dibromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; dichloromethane; dimethyl sulfoxide; benzene; 5.1: Michael addition / 10.1: Takai reaction / 13.1: Nozaki-Hiyama-Kishi coupling;
DOI:10.1002/anie.200351750

Reference yield:

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

: 658080-36-5
(4E,9E)-(3S,6S,8S,11S,13S)-6-Benzyloxy-11-hydroxy-3,8,13-trimethyl-2,3,6,7,8,11,12,13-octahydro-cyclopentacyclododecen-1-one

Guidance literature:: Multi-step reaction with 14 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

14.1: 14 percent / CrCl₂; NiCl₂ / dimethylsulfoxide / 24 h / 50 °C

With chromium dichloride; dipyridinium dichromate; n-butyllithium; formic acid; samarium diiodide; trichloroisocyanuric acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; nickel dichloride; zinc dibromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; dichloromethane; dimethyl sulfoxide; benzene; 6.1: Michael addition / 11.1: Takai reaction / 14.1: Nozaki-Hiyama-Kishi coupling;
DOI:10.1002/anie.200351750