1-[(tert-butyldimethylsilyl)oxy]-23,25-(isopropylidenedioxy)-24-oxo-19-nor-vitamin D₃ tert-butyldimethylsilyl ether

Base Information

• Chemical Name: 1-[(tert-butyldimethylsilyl)oxy]-23,25-(isopropylidenedioxy)-24-oxo-19-nor-vitamin D₃ tert-butyldimethylsilyl ether
• CAS No.: 271796-47-5
• Molecular Formula: C₄₁H₇₄O₅Si₂
• Molecular Weight: 703.207

Synonyms:1-[(tert-butyldimethylsilyl)oxy]-23,25-(isopropylidenedioxy)-24-oxo-19-nor-vitamin D₃ tert-butyldimethylsilyl ether

Chemical Property of 1-[(tert-butyldimethylsilyl)oxy]-23,25-(isopropylidenedioxy)-24-oxo-19-nor-vitamin D₃ tert-butyldimethylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(tert-butyldimethylsilyl)oxy]-23,25-(isopropylidenedioxy)-24-oxo-19-nor-vitamin D₃ tert-butyldimethylsilyl ether

There total 12 articles about 1-[(tert-butyldimethylsilyl)oxy]-23,25-(isopropylidenedioxy)-24-oxo-19-nor-vitamin D₃ 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: 80.0%

(1R,3R)-1,3-bis((tert-butyldimethyl)silanyloxy)-5-[2-(diphenylphosphinoyl)-ethylidene]cyclohexane (139356-39-1) + De-A,B-24-oxo-23,25-(isopropylidenedioxy)cholestan-8-one (189894-17-5) → 1-[(tert-butyldimethylsilyl)oxy]-23,25-(isopropylidenedioxy)-24-oxo-19-nor-vitamin D3 tert-butyldimethylsilyl ether (271796-47-5)

Guidance literature:

(1R,3R)-1,3-bis((tert-butyldimethyl)silanyloxy)-5-[2-(diphenylphosphinoyl)-ethylidene]cyclohexane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

De-A,B-24-oxo-23,25-(isopropylidenedioxy)cholestan-8-one; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 5.5h;

DOI:10.1016/S0039-128X(99)00110-5

Reference yield:

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol (64190-52-9) → 1-[(tert-butyldimethylsilyl)oxy]-23,25-(isopropylidenedioxy)-24-oxo-19-nor-vitamin D3 tert-butyldimethylsilyl ether (271796-47-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 97 percent / Ph₃P; imidazole; I₂ / benzene / 3 h / 20 °C

2.1: 94 percent / dimethylformamide

3.1: 100 percent / Hunig's base / CH₂Cl₂ / 20 °C

4.1: diisopropylamine; tetramethylenediamine; n-BuLi / tetrahydrofuran; hexane / 0.25 h / -20 °C

4.2: 81 percent / tetrahydrofuran; hexane / 5 h

5.1: 86 percent / 5 percent Na/Hg; Na₂HPO₄ / methanol / 1 h / 0 °C

6.1: 71 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2.25 h / -78 - -10 °C

7.1: LDA / tetrahydrofuran; hexane / 0.08 h / -20 °C

7.2: tetrahydrofuran; hexane / 3.5 h / 0 °C

8.1: chloroperbenzoic acid / CH₂Cl₂ / 4 h / 0 °C

9.1: 78 percent / pyridinium p-toluenesulfonate / dimethylformamide / 48 h

10.1: 95 percent / H₂ / 10 percent Pd/C / ethanol

11.1: 96 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2.75 h / -78 - -10 °C

12.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

12.2: 80 percent / tetrahydrofuran; hexane / 5.5 h / -78 - 20 °C

With 1H-imidazole; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; hydrogen; iodine; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: Iodination / 2.1: sulfonylation / 3.1: Etherification / 4.1: Metallation / 4.2: Ring cleavage / 5.1: Hydrogenolysis / 6.1: Oxidation / 7.1: Metallation / 7.2: silylation / 8.1: Oxidation / 9.1: ketalization / 10.1: Hydrogenolysis / 11.1: Oxidation / 12.1: Metallation / 12.2: olefination;

DOI:10.1016/S0039-128X(99)00110-5

Reference yield:

(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol (116535-65-0) → 1-[(tert-butyldimethylsilyl)oxy]-23,25-(isopropylidenedioxy)-24-oxo-19-nor-vitamin D3 tert-butyldimethylsilyl ether (271796-47-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 94 percent / dimethylformamide

2.1: 100 percent / Hunig's base / CH₂Cl₂ / 20 °C

3.1: diisopropylamine; tetramethylenediamine; n-BuLi / tetrahydrofuran; hexane / 0.25 h / -20 °C

3.2: 81 percent / tetrahydrofuran; hexane / 5 h

4.1: 86 percent / 5 percent Na/Hg; Na₂HPO₄ / methanol / 1 h / 0 °C

5.1: 71 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2.25 h / -78 - -10 °C

6.1: LDA / tetrahydrofuran; hexane / 0.08 h / -20 °C

6.2: tetrahydrofuran; hexane / 3.5 h / 0 °C

7.1: chloroperbenzoic acid / CH₂Cl₂ / 4 h / 0 °C

8.1: 78 percent / pyridinium p-toluenesulfonate / dimethylformamide / 48 h

9.1: 95 percent / H₂ / 10 percent Pd/C / ethanol

10.1: 96 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2.75 h / -78 - -10 °C

11.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

11.2: 80 percent / tetrahydrofuran; hexane / 5.5 h / -78 - 20 °C

With disodium hydrogenphosphate; sodium amalgam; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; hydrogen; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: sulfonylation / 2.1: Etherification / 3.1: Metallation / 3.2: Ring cleavage / 4.1: Hydrogenolysis / 5.1: Oxidation / 6.1: Metallation / 6.2: silylation / 7.1: Oxidation / 8.1: ketalization / 9.1: Hydrogenolysis / 10.1: Oxidation / 11.1: Metallation / 11.2: olefination;

DOI:10.1016/S0039-128X(99)00110-5

upstream raw materials:

(1R,3R)-1,3-bis((tert-butyldimethyl)silanyloxy)-5-[2-(diphenylphosphinoyl)-ethylidene]cyclohexane

De-A,B-24-oxo-23,25-(isopropylidenedioxy)cholestan-8-one

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

(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 271796-47-5 1-[(tert-butyldimethylsilyl)oxy]-23,25-(isopropylidenedioxy)-24-oxo-19-nor-vitamin D₃ tert-butyldimethylsilyl ether

Send

Send

Metric Ton KG G Pound L ML

Send

Send