(1R,3S,5Z)-4-methylene-5-{(2E)-2-{(1R,3aS,7R,7aR)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7-(7-hydroxy-7-methyloctyl)-7a-methyl-4H-inden-4-ylidene}ethylidene}cyclohexane-1,3-diol

Base Information

• Chemical Name: (1R,3S,5Z)-4-methylene-5-{(2E)-2-{(1R,3aS,7R,7aR)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7-(7-hydroxy-7-methyloctyl)-7a-methyl-4H-inden-4-ylidene}ethylidene}cyclohexane-1,3-diol
• CAS No.: 1412439-04-3
• Molecular Formula: C₃₆H₆₂O₄
• Molecular Weight: 558.886

Synonyms:(1R,3S,5Z)-4-methylene-5-{(2E)-2-{(1R,3aS,7R,7aR)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7-(7-hydroxy-7-methyloctyl)-7a-methyl-4H-inden-4-ylidene}ethylidene}cyclohexane-1,3-diol

Chemical Property of (1R,3S,5Z)-4-methylene-5-{(2E)-2-{(1R,3aS,7R,7aR)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7-(7-hydroxy-7-methyloctyl)-7a-methyl-4H-inden-4-ylidene}ethylidene}cyclohexane-1,3-diol

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Technology Process of (1R,3S,5Z)-4-methylene-5-{(2E)-2-{(1R,3aS,7R,7aR)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7-(7-hydroxy-7-methyloctyl)-7a-methyl-4H-inden-4-ylidene}ethylidene}cyclohexane-1,3-diol

There total 7 articles about (1R,3S,5Z)-4-methylene-5-{(2E)-2-{(1R,3aS,7R,7aR)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7-(7-hydroxy-7-methyloctyl)-7a-methyl-4H-inden-4-ylidene}ethylidene}cyclohexane-1,3-diol 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%

C48H90O4Si2 (1412439-03-2) → (1R,3S,5Z)-4-methylene-5-{(2E)-2-{(1R,3aS,7R,7aR)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7-(7-hydroxy-7-methyloctyl)-7a-methyl-4H-inden-4-ylidene}ethylidene}cyclohexane-1,3-diol (1412439-04-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 20h; Inert atmosphere; Darkness;

DOI:10.1002/hlca.201200427

Reference yield:

12β-(7-hydroxy-7-methyloctyl)-de-A,B-23,24-dinorcholan-8β,22-diol (1402432-18-1) → (1R,3S,5Z)-4-methylene-5-{(2E)-2-{(1R,3aS,7R,7aR)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7-(7-hydroxy-7-methyloctyl)-7a-methyl-4H-inden-4-ylidene}ethylidene}cyclohexane-1,3-diol (1412439-04-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triphenylphosphine; 1H-imidazole; iodine / tetrahydrofuran / 2 h / -20 - 20 °C / Inert atmosphere

2.1: pyridine; zinc; nickel(II) chloride hexahydrate / 2 h / 60 °C / Inert atmosphere

2.2: 0.33 h / 20 °C / Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 1 h / Inert atmosphere; Darkness

4.1: tetrahydrofuran; toluene / 5 h / -17 - 20 °C / Inert atmosphere

5.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; tricyclohexylphosphine; potassium acetate / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere

6.1: potassium phosphate; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 1 h / Inert atmosphere; Darkness

6.2: Inert atmosphere

7.1: diethyl ether / 1.25 h / -78 - 20 °C / Inert atmosphere; Darkness

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 h / Inert atmosphere; Darkness

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; nickel(II) chloride hexahydrate; tetrabutyl ammonium fluoride; iodine; potassium acetate; Dess-Martin periodane; triphenylphosphine; zinc; tricyclohexylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; 4.1: |Wittig Olefination / 6.1: |Suzuki-Miyaura Coupling;

DOI:10.1002/hlca.201200427

Reference yield:

7-((3R,3aR,4R,7S,7aR)-octahydro-3-[(1S)-2-iodo-1-methylethyl]-3a-methyl-1H-indene-4-yl)-α,α-dimethylheptanol (1412438-97-1) → (1R,3S,5Z)-4-methylene-5-{(2E)-2-{(1R,3aS,7R,7aR)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7-(7-hydroxy-7-methyloctyl)-7a-methyl-4H-inden-4-ylidene}ethylidene}cyclohexane-1,3-diol (1412439-04-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine; zinc; nickel(II) chloride hexahydrate / 2 h / 60 °C / Inert atmosphere

1.2: 0.33 h / 20 °C / Inert atmosphere

2.1: Dess-Martin periodane / dichloromethane / 1 h / Inert atmosphere; Darkness

3.1: tetrahydrofuran; toluene / 5 h / -17 - 20 °C / Inert atmosphere

4.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; tricyclohexylphosphine; potassium acetate / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere

5.1: potassium phosphate; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 1 h / Inert atmosphere; Darkness

5.2: Inert atmosphere

6.1: diethyl ether / 1.25 h / -78 - 20 °C / Inert atmosphere; Darkness

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 h / Inert atmosphere; Darkness

With pyridine; bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; nickel(II) chloride hexahydrate; tetrabutyl ammonium fluoride; potassium acetate; Dess-Martin periodane; zinc; tricyclohexylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; 3.1: |Wittig Olefination / 5.1: |Suzuki-Miyaura Coupling;

DOI:10.1002/hlca.201200427

upstream raw materials:

C₄₈H₉₀O₄Si₂

12β-(7-hydroxy-7-methyloctyl)-de-A,B-23,24-dinorcholan-8β,22-diol

7-((3R,3aR,4R,7S,7aR)-octahydro-3-[(1S)-2-iodo-1-methylethyl]-3a-methyl-1H-indene-4-yl)-α,α-dimethylheptanol

methyl (δR,1R,3aR,4S,7R,7aR)-octahydro-4-hydroxy-7-(7-hydroxy-7-methyloctyl)-δ,7a-dimethyl-1H-indene-1-pentanoate

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