(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}-pentan-2-ol

Base Information

• Chemical Name: (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}-pentan-2-ol
• CAS No.: 167892-98-0
• Molecular Formula: C₃₆H₆₆O₃Si₂
• Molecular Weight: 603.089
• Mol file: 167892-98-0.mol

Synonyms:(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}-pentan-2-ol

Chemical Property of (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}-pentan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (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}-pentan-2-ol

There total 1 articles about (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}-pentan-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: 91.0%

methylmagnesium bromide (75-16-1) + (5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene (143884-26-8) → (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}-pentan-2-ol (167892-98-0)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1016/S0968-0896(00)00142-5

Reference yield: 92.0%

(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}-pentan-2-ol (167892-98-0) → 1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(Z),7(E),10(19)-triene (167892-99-1)

Guidance literature:

With N-methyl-2-indolinone; 4 Angstroem MS; tetrapropylammonium perruthennate; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1016/S0968-0896(00)00142-5

Reference yield:

(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}-pentan-2-ol (167892-98-0) → (5Z,7E)-(1R,3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol

Guidance literature:

Multi-step reaction with 12 steps

1.1: 92 percent / NMO; 4 Angstroem MS / tetrapropylammonium perrutenate / CH₂Cl₂ / 0.25 h / 20 °C

2.1: 82 percent / LiN(TMS)2 / tetrahydrofuran / 0.5 h / -70 °C

3.1: 52 percent / NaBH₄ / tetrahydrofuran; methanol / 0.17 h / -10 °C

4.1: 97 percent / pyridine / 12 h / 20 °C

5.1: 89 percent / iPr₂NEt / CHCl₃ / 1 h / Heating

6.1: 94 percent / 5 percent KOH / methanol / 1 h / 0 °C

7.1: NaH; imidazole / tetrahydrofuran / 20 °C

7.2: 80 percent / 2 h / 20 °C

8.1: 97 percent / nBu₃SnH / toluene / 1 h / Heating

9.1: 56 percent / MsOH / methanol / 2 h / 20 °C

10.1: 66 percent / Dess-Martin periodinane / acetonitrile / 4 h / 20 °C

11.1: 66 percent / NaBH₄ / methanol / 1.5 h / 0 °C

12.1: 82 percent / acetone / 6 h / 80 °C

With 1H-imidazole; potassium hydroxide; sodium tetrahydroborate; N-methyl-2-indolinone; methanesulfonic acid; 4 Angstroem MS; tri-n-butyl-tin hydride; sodium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; tetrapropylammonium perruthennate; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; acetone; toluene; acetonitrile; 1.1: Oxidation / 2.1: Condensation / 3.1: Reduction / 4.1: Acetylation / 5.1: Alkylation / 6.1: Deacetylation / 7.1: thiocarbonylation / 7.2: Methylation / 8.1: Reduction / 9.1: Hydrolysis / 10.1: Oxidation / 11.1: Reduction / 12.1: Isomerization;

DOI:10.1016/S0968-0896(00)00142-5

upstream raw materials:

methylmagnesium bromide

(5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene

Downstream raw materials:

1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(Z),7(E),10(19)-triene

Falecalcitriol

1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-secocholesta-5(Z),7(E),10(19)-trien-23(R),25-diol