(R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

Base Information

Chemical Name:(R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol
CAS No.:794516-08-8
Molecular Formula:C₄₇H₉₀O₅Si₃
Molecular Weight:819.485
Hs Code.:

(R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

Synonyms:(R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

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Chemical Property of (R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

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Technology Process of (R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

There total 14 articles about (R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol 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: 75.0%

: 143705-63-9
(E)-(20R)-de-A,B-8-(bromomethylene)cholestan-25-ol

: 299410-90-5
(3R,4S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-[2-(tert-butyldimethylsilyloxy)ethoxy]oct-1-en-7-yne

: 794516-08-8
(R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In toluene; Heating;
DOI:10.1021/ol006222j

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 794516-08-8
(R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

2: 75 percent / Pd(PPh₃)4; Et₃N / toluene / Heating

With 2,6-dimethylpyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In dichloromethane; toluene; 1: Substitution / 2: Cyclization;
DOI:10.1021/ol006222j

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 794516-08-8
(R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 93 percent / imidazole / dimethylformamide

2.1: 71 percent / NBS; BaCO₃ / CCl₄ / 0.58 h / Heating

3.1: 95 percent / NaOMe / methanol

4.1: 93 percent / imidazole / dimethylformamide

5.1: Bu₄NF / tetrahydrofuran

6.1: Zn; NaBH₃CN / propan-1-ol; H₂O / 0.75 h / 95 °C

6.2: 71 percent / NaBH₄

7.1: TmCl; DMAP / CH₂Cl₂

7.2: LiHMDS / tetrahydrofuran / -78 - 20 °C

8.1: 91 percent / BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

9.1: 93 percent / K₂CO₃ / methanol

10.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

11.1: 75 percent / Pd(PPh₃)4; Et₃N / toluene / Heating

With 1H-imidazole; 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; sodium cyanoborohydride; potassium carbonate; triethylamine; barium carbonate; zinc; In tetrahydrofuran; methanol; propan-1-ol; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Substitution / 2.1: Bromination / 3.1: deacylation / 4.1: Substitution / 5.1: Substitution / 6.1: Ring cleavage / 6.2: Reduction / 7.1: Substitution / 7.2: Cyclization / 8.1: Ring cleavage / 9.1: Substitution / 10.1: Substitution / 11.1: Cyclization;
DOI:10.1021/ol006222j