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

Base Information

• Chemical Name: (S)-4-((R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentyl)-2,2,4-trimethyl-[1,3]dioxolane
• CAS No.: 93511-78-5
• Molecular Formula: C₄₂H₇₆O₄Si₂
• Molecular Weight: 701.234

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

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

Chemical Property:

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

There total 37 articles about (S)-4-((R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentyl)-2,2,4-trimethyl-[1,3]dioxolane 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:

<1R-<1β(R*,S*,S*),3aα,4β,7aβ>>-6-(octahydro-4-hydroxy-7a-methyl-1H-inden-1-yl)-4-dimethylamino-2-methylheptane-1,2-diol (93489-63-5) → (S)-4-((R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentyl)-2,2,4-trimethyl-[1,3]dioxolane (93511-78-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 2.2 g / toluenesulfonic acid monohydrate / acetone / 25 h / Ambient temperature

2: 2.97 g / diethyl ether / 19 h / Ambient temperature

3: KOH / ethanol / 23 h / Heating

4: 1.) toluenesulfonic acid monohydrate; 2.) MeOH / 1.) RT, 50 min; 2.) RT, 45 min

5: H₂ / 10 percent Pd/C / ethyl acetate

6: 90 percent / 2,2'- bipyridinium chlorochromate, anhyd. NaOAc / CH₂Cl₂ / 4.5 h / Ambient temperature

7: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min; 2.) THF, -78 deg C, 2,5 h

With methanol; potassium hydroxide; n-butyllithium; hydrogen; sodium acetate; toluene-4-sulfonic acid; 2,2'-bipyridinium chlorochromate; palladium on activated charcoal; toluene-4-sulfonic acid; In diethyl ether; ethanol; dichloromethane; ethyl acetate; acetone;

DOI:10.1016/0040-4020(84)80011-3

Reference yield:

(3S,5S)-3-[(R)-2-((1R,3aR,4S,7aR)-4-Hydroxy-7a-methyl-octahydro-inden-1-yl)-propyl]-5-methoxycarbonyl-2,2,5-trimethyl-isoxazolidin-2-ium; iodide (93489-62-4) → (S)-4-((R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentyl)-2,2,4-trimethyl-[1,3]dioxolane (93511-78-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) LAH; 2.) 10 percent NaOH / 1.) THF, 20 deg C, 0.5 h, rt, 15 min; reflux 2 h; 2.) water, 15 deg C, 0.25 h

2: 2.2 g / toluenesulfonic acid monohydrate / acetone / 25 h / Ambient temperature

3: 2.97 g / diethyl ether / 19 h / Ambient temperature

4: KOH / ethanol / 23 h / Heating

5: 1.) toluenesulfonic acid monohydrate; 2.) MeOH / 1.) RT, 50 min; 2.) RT, 45 min

6: H₂ / 10 percent Pd/C / ethyl acetate

7: 90 percent / 2,2'- bipyridinium chlorochromate, anhyd. NaOAc / CH₂Cl₂ / 4.5 h / Ambient temperature

8: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min; 2.) THF, -78 deg C, 2,5 h

With methanol; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; hydrogen; sodium acetate; toluene-4-sulfonic acid; 2,2'-bipyridinium chlorochromate; palladium on activated charcoal; toluene-4-sulfonic acid; In diethyl ether; ethanol; dichloromethane; ethyl acetate; acetone;

DOI:10.1016/0040-4020(84)80011-3

Reference yield:

[(1S,3R)-3-((1R,3aR,4S,7aR)-4-Hydroxy-7a-methyl-octahydro-inden-1-yl)-1-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-ylmethyl)-butyl]-trimethyl-ammonium; iodide → (S)-4-((R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentyl)-2,2,4-trimethyl-[1,3]dioxolane (93511-78-5)

Guidance literature:

Multi-step reaction with 5 steps

1: KOH / ethanol / 23 h / Heating

2: 1.) toluenesulfonic acid monohydrate; 2.) MeOH / 1.) RT, 50 min; 2.) RT, 45 min

3: H₂ / 10 percent Pd/C / ethyl acetate

4: 90 percent / 2,2'- bipyridinium chlorochromate, anhyd. NaOAc / CH₂Cl₂ / 4.5 h / Ambient temperature

5: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min; 2.) THF, -78 deg C, 2,5 h

With methanol; potassium hydroxide; n-butyllithium; hydrogen; sodium acetate; toluene-4-sulfonic acid; 2,2'-bipyridinium chlorochromate; palladium on activated charcoal; In ethanol; dichloromethane; ethyl acetate;

DOI:10.1016/0040-4020(84)80011-3

upstream raw materials:

<1R-<1β(R*,S*),3aα,7aβ>>-octahydro-7a-methyl-1-<1-methyl-4-<(2,2,4-trimethyl)-1,3-dioxolan-4-yl>butyl>-4H-inden-4-one

C₃₃H₅₁O₃PSi₂^(1-)

<3aR-(3aα,4β,7aβ)>-7a-methyl-4-hydroxy-octahydro-1H-inden-1-one

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

Downstream raw materials:

(25S)-1α,25,26-trihydroxycholecalciferol

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