6-(4-{2-[5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene}-7a-methyl-octahydro-inden-1-yl)-2-methyl-heptan-2-ol

Base Information

• Chemical Name: 6-(4-{2-[5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene}-7a-methyl-octahydro-inden-1-yl)-2-methyl-heptan-2-ol
• CAS No.: 140710-90-3
• Molecular Formula: C33H58 O2 Si
• Molecular Weight: 514.908
• Mol file: 140710-90-3.mol

Synonyms:6-(4-{2-[5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene}-7a-methyl-octahydro-inden-1-yl)-2-methyl-heptan-2-ol

Chemical Property of 6-(4-{2-[5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene}-7a-methyl-octahydro-inden-1-yl)-2-methyl-heptan-2-ol

Chemical Property:

• Refractive Index: 1.508
• PSA: 29.46000
• LogP: 9.76340

Purity/Quality:

95% ^*data from raw suppliers

3-O-tert-ButyldimethylsilylCalcifediol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A protected Calcifediol (C125700), a hydroxylated metabolite of Vitamin D3.

Technology Process of 6-(4-{2-[5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene}-7a-methyl-octahydro-inden-1-yl)-2-methyl-heptan-2-ol

There total 15 articles about 6-(4-{2-[5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene}-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: 89.0%

calcidiol (19356-17-3) + tert-butyldimethylsilyl chloride (18162-48-6) → (R)-6-{(1R,3aS,7aR)-4-[2-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol (140710-90-3)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1039/c6ra02965e

Reference yield: 78.0%

methyl magnesium iodide (917-64-6) + C32H54O3Si → 25-hydroxy-5E-[6,19,19'-H3]vitamin D3-3β-tert-butyldimethylsilyl ether (140710-90-3)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; for 3h; Inert atmosphere;

Reference yield:

(S)-3-[(R)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ6-benzo[c]thiophen-5-ol (73809-11-7,73824-80-3,87237-31-8,87237-32-9) → (R)-6-{(1R,3aS)-4-[2-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol (140710-90-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NaHCO₃ / ethanol / Heating

2: imidazole / dimethylformamide

With 1H-imidazole; sodium hydrogencarbonate; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00359a061

upstream raw materials:

(S)-(Z)-{2-[5-(tert-butyldimethylsiloxy)-2-methylenecyclohexylidene]ethyl}diphenylphosphine oxide

des-A,B-25-(ethoxymethyloxy)cholestan-8-one

calcidiol

tert-butyldimethylsilyl chloride

Downstream raw materials:

1α,25-di-tetrahydropyranyloxy-3β-tert-butyldimethysilyl-5Z-vitamin D3

1α,25-di-tetrahydropyranyloxy-5Z-vitamin D3

C₃₉H₆₁BrO₆

1α-[((trimethylsilyl)-oxy)]-3β-[((tertiary-butyl-dimethylsilyl)-oxy)], 25-trihydroxy-9,10-5(Z),7(E),10(19)-triene