24-epi-26,26,26,27,27,27-hexafluoro-1α,25-dihydroxyvitamin D₂ bis(tert-butyldimethylsilyl)ether

Base Information

• Chemical Name: 24-epi-26,26,26,27,27,27-hexafluoro-1α,25-dihydroxyvitamin D₂ bis(tert-butyldimethylsilyl)ether
• CAS No.: 156078-62-5
• Molecular Formula: C₄₀H₆₆F₆O₃Si₂
• Molecular Weight: 765.124
• Mol file: 156078-62-5.mol

Synonyms:24-epi-26,26,26,27,27,27-hexafluoro-1α,25-dihydroxyvitamin D₂ bis(tert-butyldimethylsilyl)ether

Chemical Property of 24-epi-26,26,26,27,27,27-hexafluoro-1α,25-dihydroxyvitamin D₂ bis(tert-butyldimethylsilyl)ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 24-epi-26,26,26,27,27,27-hexafluoro-1α,25-dihydroxyvitamin D₂ bis(tert-butyldimethylsilyl)ether

There total 13 articles about 24-epi-26,26,26,27,27,27-hexafluoro-1α,25-dihydroxyvitamin D₂ bis(tert-butyldimethylsilyl)ether 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,3aR,4S,7aR)-7a-methyl-1-<(2E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl>-octahydro-1H-inden-4-ol (55812-82-3,63730-57-4,63730-58-5,102281-42-5) → 24-epi-26,26,26,27,27,27-hexafluoro-1α,25-dihydroxyvitamin D2 bis(tert-butyldimethylsilyl)ether (156078-62-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 30 h / Ambient temperature

2: 1.) O₃, pyridine, 2.) Zn, AcOH / 1.) CH₂Cl₂, -78 deg C, 50 min, 2.) CH₂Cl₂, a) -78 deg C, 30 min, b) 0 deg C, 30 min

3: 1.) BuLi, 2.) MgBr₂*OEt₂

4: 22 percent / 5percent Na-Hg, Na₂HPO₄ / tetrahydrofuran; methanol / 3 h / 0 °C

5: concd. HCl / dioxane / 0.25 h / 60 °C

6: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

7: 1.) BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -40 deg C, 1 h

With pyridine; hydrogenchloride; dmap; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; ozone; acetic acid; triethylamine; pyridinium chlorochromate; magnesium bromide; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1248/cpb.43.1897

Reference yield:

<1R-(1α,3aβ,4α,7aα)>-4-acetoxyoctahydro-1-<(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl>-7a-methyl-1H-indene (172227-33-7) → 24-epi-26,26,26,27,27,27-hexafluoro-1α,25-dihydroxyvitamin D2 bis(tert-butyldimethylsilyl)ether (156078-62-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) O₃, pyridine, 2.) Zn, AcOH / 1.) CH₂Cl₂, -78 deg C, 50 min, 2.) CH₂Cl₂, a) -78 deg C, 30 min, b) 0 deg C, 30 min

2: 1.) BuLi, 2.) MgBr₂*OEt₂

3: 22 percent / 5percent Na-Hg, Na₂HPO₄ / tetrahydrofuran; methanol / 3 h / 0 °C

4: concd. HCl / dioxane / 0.25 h / 60 °C

5: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

6: 1.) BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -40 deg C, 1 h

With pyridine; hydrogenchloride; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; ozone; acetic acid; pyridinium chlorochromate; magnesium bromide; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1248/cpb.43.1897

Reference yield:

<1R-<1α(S*),3aβ,4α,7aα>>-4-acetoxyoctahydro-α,7a-dimethyl-1H-indene-1-acetaldehyde (101262-49-1) → 24-epi-26,26,26,27,27,27-hexafluoro-1α,25-dihydroxyvitamin D2 bis(tert-butyldimethylsilyl)ether (156078-62-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) BuLi, 2.) MgBr₂*OEt₂

2: 22 percent / 5percent Na-Hg, Na₂HPO₄ / tetrahydrofuran; methanol / 3 h / 0 °C

3: concd. HCl / dioxane / 0.25 h / 60 °C

4: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

5: 1.) BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -40 deg C, 1 h

With hydrogenchloride; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; pyridinium chlorochromate; magnesium bromide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1248/cpb.43.1897

upstream raw materials:

(1R,3aR,4S,7aR)-7a-methyl-1-<(2E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl>-octahydro-1H-inden-4-ol

<1R-(1α,3aβ,4α,7aα)>-4-acetoxyoctahydro-1-<(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl>-7a-methyl-1H-indene

<1R-<1α(S^*),3aβ,4α,7aα>>-4-acetoxyoctahydro-α,7a-dimethyl-1H-indene-1-acetaldehyde

(R)-4,4,4-trifluoro-3-<(methoxymethyl)oxy>-2-methyl-3-trifluoromethylbutan-1-ol