(1R,3aS,7aS)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-isopropyl-7a-(5-methyl-5-trimethylsilanyloxy-hex-2-ynyloxymethyl)-octahydro-indene

Base Information

• Chemical Name: (1R,3aS,7aS)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-isopropyl-7a-(5-methyl-5-trimethylsilanyloxy-hex-2-ynyloxymethyl)-octahydro-indene
• CAS No.: 220173-61-5
• Molecular Formula: C₄₄H₈₀O₄Si₃
• Molecular Weight: 757.373

Synonyms:

Chemical Property of (1R,3aS,7aS)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-isopropyl-7a-(5-methyl-5-trimethylsilanyloxy-hex-2-ynyloxymethyl)-octahydro-indene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3aS,7aS)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-isopropyl-7a-(5-methyl-5-trimethylsilanyloxy-hex-2-ynyloxymethyl)-octahydro-indene

There total 11 articles about (1R,3aS,7aS)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-isopropyl-7a-(5-methyl-5-trimethylsilanyloxy-hex-2-ynyloxymethyl)-octahydro-indene 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: 70.0%

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (81522-68-1) + (1R,3aR,7aS)-1-Isopropyl-7a-(5-methyl-5-trimethylsilanyloxy-hex-2-ynyloxymethyl)-octahydro-inden-4-one (220173-60-4) → (1R,3aS,7aS)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-isopropyl-7a-(5-methyl-5-trimethylsilanyloxy-hex-2-ynyloxymethyl)-octahydro-indene (220173-61-5)

Guidance literature:

DOI:10.1016/S0968-0896(98)00161-8

Reference yield:

(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate (66774-80-9,111924-49-3) → (1R,3aS,7aS)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-isopropyl-7a-(5-methyl-5-trimethylsilanyloxy-hex-2-ynyloxymethyl)-octahydro-indene (220173-61-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 93 percent / LiAlH₄ / tetrahydrofuran / 21 h / Heating

2: 88 percent / lead tetraacetate, pyridine / benzene / 3.5 h / 15 °C / Irradiation

3: 39 percent / boron trifluoride etherate / -20 deg C, 45 min, room temperature, 1 h

4: 65 percent / potassium hydroxide / methanol / 2.5 h / Heating

5: 94 percent / imidazole / dimethylformamide / 4 h / Ambient temperature

6: 50 percent / potassium tert-butoxide, 18-crown-6 / tetrahydrofuran / 19 h / Ambient temperature

7: 45 percent / n-butyllithium, boron trifluoride diethyletherate / tetrahydrofuran; hexane / -78 - 20 °C

8: 85 percent / hydrofluoric acid / ethyl acetate; acetonitrile; H₂O / 0.67 h / Ambient temperature

9: 81 percent / pyridinium dichromate / CH₂Cl₂ / 18 h / Ambient temperature

10: 34 percent / N-ethyldiisopropylamine / CH₂Cl₂ / 2.33 h / Ambient temperature

11: 70 percent

With pyridine; 1H-imidazole; lead(IV) acetate; potassium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; 18-crown-6 ether; boron trifluoride diethyl etherate; hydrogen fluoride; potassium tert-butylate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0968-0896(98)00161-8

Reference yield:

20-methyl-de-A,B-pregnan-(8S)-ol (197647-61-3) → (1R,3aS,7aS)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-isopropyl-7a-(5-methyl-5-trimethylsilanyloxy-hex-2-ynyloxymethyl)-octahydro-indene (220173-61-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 88 percent / lead tetraacetate, pyridine / benzene / 3.5 h / 15 °C / Irradiation

2: 39 percent / boron trifluoride etherate / -20 deg C, 45 min, room temperature, 1 h

3: 65 percent / potassium hydroxide / methanol / 2.5 h / Heating

4: 94 percent / imidazole / dimethylformamide / 4 h / Ambient temperature

5: 50 percent / potassium tert-butoxide, 18-crown-6 / tetrahydrofuran / 19 h / Ambient temperature

6: 45 percent / n-butyllithium, boron trifluoride diethyletherate / tetrahydrofuran; hexane / -78 - 20 °C

7: 85 percent / hydrofluoric acid / ethyl acetate; acetonitrile; H₂O / 0.67 h / Ambient temperature

8: 81 percent / pyridinium dichromate / CH₂Cl₂ / 18 h / Ambient temperature

9: 34 percent / N-ethyldiisopropylamine / CH₂Cl₂ / 2.33 h / Ambient temperature

10: 70 percent

With pyridine; 1H-imidazole; lead(IV) acetate; potassium hydroxide; dipyridinium dichromate; n-butyllithium; 18-crown-6 ether; boron trifluoride diethyl etherate; hydrogen fluoride; potassium tert-butylate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0968-0896(98)00161-8

upstream raw materials:

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

(1R,3aR,7aS)-1-Isopropyl-7a-(5-methyl-5-trimethylsilanyloxy-hex-2-ynyloxymethyl)-octahydro-inden-4-one

(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate

20-methyl-de-A,B-pregnan-(8S)-ol

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