(R)-8-{(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}-2-methyl-nonan-2-ol

Base Information

• Chemical Name: (R)-8-{(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}-2-methyl-nonan-2-ol
• CAS No.: 128387-25-7
• Molecular Formula: C₄₁H₇₆O₃Si₂
• Molecular Weight: 673.224
• Mol file: 128387-25-7.mol

Synonyms:(R)-8-{(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}-2-methyl-nonan-2-ol

Chemical Property of (R)-8-{(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}-2-methyl-nonan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-8-{(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}-2-methyl-nonan-2-ol

There total 7 articles about (R)-8-{(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}-2-methyl-nonan-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:

tert-butyldimethylsilyl chloride (18162-48-6) → (R)-8-{(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}-2-methyl-nonan-2-ol (128387-25-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / imidazole / dimethylformamide / 2.5 h / Ambient temperature

2: 91 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

3: 87 percent / Et₃N, N,N-dimethylaminopyridine / CH₂Cl₂ / 16 h / Ambient temperature

4: 1.) Li₂CO₃, LiBr / 1.) DMF, 80 deg C, 1 h, 2.) DMF, 80 deg C, 2 h

5: 1.) n-BuLi, 2.) hexamethylphosphoric triamide

6: 1.) Na₂HPO₄, 2.) 5percent Na/Hg / 1.) MeOH, RT, 20 min, 2.) MeOH, RT, 4 h

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; lithium carbonate; triethylamine; lithium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0039-128X(97)00040-8

Reference yield:

1α-[(tert-butyldimethylsilyl)oxy]-24-(methoxycarbonyl)-25,26,27-trisnorvitamin D3 tert-butyldimethylsilyl ether (145372-43-6) → (R)-8-{(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}-2-methyl-nonan-2-ol (128387-25-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

2: 87 percent / Et₃N, N,N-dimethylaminopyridine / CH₂Cl₂ / 16 h / Ambient temperature

3: 1.) Li₂CO₃, LiBr / 1.) DMF, 80 deg C, 1 h, 2.) DMF, 80 deg C, 2 h

4: 1.) n-BuLi, 2.) hexamethylphosphoric triamide

5: 1.) Na₂HPO₄, 2.) 5percent Na/Hg / 1.) MeOH, RT, 20 min, 2.) MeOH, RT, 4 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; lithium carbonate; triethylamine; lithium bromide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0039-128X(97)00040-8

Reference yield:

(5Z,7E)-(1S,3R)-1,3-dihydroxy-23a-homo-9,10-secochola-5,7,10(19)-trien-24-oic acid methyl ester (74029-72-4) → (R)-8-{(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}-2-methyl-nonan-2-ol (128387-25-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / imidazole / dimethylformamide / 2.5 h / Ambient temperature

2: 91 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

3: 87 percent / Et₃N, N,N-dimethylaminopyridine / CH₂Cl₂ / 16 h / Ambient temperature

4: 1.) Li₂CO₃, LiBr / 1.) DMF, 80 deg C, 1 h, 2.) DMF, 80 deg C, 2 h

5: 1.) n-BuLi, 2.) hexamethylphosphoric triamide

6: 1.) Na₂HPO₄, 2.) 5percent Na/Hg / 1.) MeOH, RT, 20 min, 2.) MeOH, RT, 4 h

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; lithium carbonate; triethylamine; lithium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0039-128X(97)00040-8

upstream raw materials:

(R)-4-Benzenesulfonyl-8-{(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}-2-methyl-nonan-2-ol

tert-butyldimethylsilyl chloride

1α-[(tert-butyldimethylsilyl)oxy]-24-(methoxycarbonyl)-25,26,27-trisnorvitamin D3 tert-butyldimethylsilyl ether

(5Z,7E)-(1S,3R)-1,3-dihydroxy-23a-homo-9,10-secochola-5,7,10⁽¹⁹⁾-trien-24-oic acid methyl ester

Downstream raw materials:

PRI-1890