1α,24-dihydroxy-12β-(7-hydroxy-7-methyloctyl)-25,26,27-trinorvitamin D3

Base Information

• Chemical Name: 1α,24-dihydroxy-12β-(7-hydroxy-7-methyloctyl)-25,26,27-trinorvitamin D3
• CAS No.: 1402432-44-3
• Molecular Formula: C₃₃H₅₆O₄
• Molecular Weight: 516.805

Synonyms:

Chemical Property of 1α,24-dihydroxy-12β-(7-hydroxy-7-methyloctyl)-25,26,27-trinorvitamin D3

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1α,24-dihydroxy-12β-(7-hydroxy-7-methyloctyl)-25,26,27-trinorvitamin D3

There total 21 articles about 1α,24-dihydroxy-12β-(7-hydroxy-7-methyloctyl)-25,26,27-trinorvitamin D3 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:

8β,22-bis(tert-butyldimethylsilyloxy)-de-A,B-23,24-dinorchol-11-en-12-yl trifluoromethanesulfonate (1402432-28-3) → 1α,24-dihydroxy-12β-(7-hydroxy-7-methyloctyl)-25,26,27-trinorvitamin D3 (1402432-44-3)

Guidance literature:

Multi-step reaction with 15 steps

1.1: bis-triphenylphosphine-palladium(II) chloride; diethylamine; copper(l) iodide / 13 h / 0 - 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 72 h / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 168 h / 55 °C / Inert atmosphere

4.1: pyridine / 24 h / 0 - 4 °C / Inert atmosphere

5.1: dimethyl sulfoxide / 2 h / 90 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane / 3 h / -15 - 0 °C / Inert atmosphere

6.2: 2 h / 5 °C / Inert atmosphere

6.3: 2 h / -78 °C / Inert atmosphere

7.1: pyridine / 0 - 4 °C / Inert atmosphere

8.1: dimethyl sulfoxide / 90 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / dichloromethane / 3 h / -15 - 0 °C / Inert atmosphere

9.2: 2 h / 5 °C / Inert atmosphere

9.3: 2 h / -78 °C / Inert atmosphere

10.1: 1H-imidazole / N,N-dimethyl-formamide / 10 h / 0 - 20 °C / Inert atmosphere

11.1: dipyridinium dichromate / dichloromethane / 20 °C / Inert atmosphere

12.1: potassium tert-butylate / tetrahydrofuran; toluene / -17 °C / Inert atmosphere

12.2: -17 - 20 °C / Inert atmosphere; Sonication

13.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; tricyclohexylphosphine; potassium acetate / dimethyl sulfoxide / 80 °C / Inert atmosphere

14.1: bis-triphenylphosphine-palladium(II) chloride; potassium phosphate / tetrahydrofuran / Inert atmosphere

15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere; Darkness

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; copper(l) iodide; dipyridinium dichromate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium 10% on activated carbon; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; potassium acetate; diisobutylaluminium hydride; diethylamine; tricyclohexylphosphine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; 12.1: |Wittig Olefination / 12.2: |Wittig Olefination / 13.1: |Miyaura Borylation Reaction / 14.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/jm3008272

Reference yield:

8β,22-bis(tert-butyldimethylsilyloxy)-12-(7-hydroxy-7-methyloct-1-ynyl)-de-A,B-23,24-dinorchol-11-ene (1402432-29-4) → 1α,24-dihydroxy-12β-(7-hydroxy-7-methyloctyl)-25,26,27-trinorvitamin D3 (1402432-44-3)

Guidance literature:

Multi-step reaction with 14 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 72 h / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 168 h / 55 °C / Inert atmosphere

3.1: pyridine / 24 h / 0 - 4 °C / Inert atmosphere

4.1: dimethyl sulfoxide / 2 h / 90 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane / 3 h / -15 - 0 °C / Inert atmosphere

5.2: 2 h / 5 °C / Inert atmosphere

5.3: 2 h / -78 °C / Inert atmosphere

6.1: pyridine / 0 - 4 °C / Inert atmosphere

7.1: dimethyl sulfoxide / 90 °C / Inert atmosphere

8.1: diisobutylaluminium hydride / dichloromethane / 3 h / -15 - 0 °C / Inert atmosphere

8.2: 2 h / 5 °C / Inert atmosphere

8.3: 2 h / -78 °C / Inert atmosphere

9.1: 1H-imidazole / N,N-dimethyl-formamide / 10 h / 0 - 20 °C / Inert atmosphere

10.1: dipyridinium dichromate / dichloromethane / 20 °C / Inert atmosphere

11.1: potassium tert-butylate / tetrahydrofuran; toluene / -17 °C / Inert atmosphere

11.2: -17 - 20 °C / Inert atmosphere; Sonication

12.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; tricyclohexylphosphine; potassium acetate / dimethyl sulfoxide / 80 °C / Inert atmosphere

13.1: bis-triphenylphosphine-palladium(II) chloride; potassium phosphate / tetrahydrofuran / Inert atmosphere

14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere; Darkness

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; dipyridinium dichromate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium 10% on activated carbon; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; potassium acetate; diisobutylaluminium hydride; tricyclohexylphosphine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; 11.1: |Wittig Olefination / 11.2: |Wittig Olefination / 12.1: |Miyaura Borylation Reaction / 13.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/jm3008272

Reference yield:

22-(tert-butyldimethylsilyloxy)-de-A,B-23,24-dinorchol-9-en-8β-ol (1402432-19-2) → 1α,24-dihydroxy-12β-(7-hydroxy-7-methyloctyl)-25,26,27-trinorvitamin D3 (1402432-44-3)

Guidance literature:

Multi-step reaction with 24 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere; Darkness

3.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diethylamine / hexane; diethyl ether / 15 h / -40 - 20 °C / Inert atmosphere

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere; Darkness

5.1: triethylamine / dichloromethane / 0.25 h / -20 °C / Inert atmosphere

5.2: 1 h / Inert atmosphere

6.1: sodium; naphthalene / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 48 h / Inert atmosphere

8.1: dipyridinium dichromate / dichloromethane / 36 h / Inert atmosphere

9.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 4 h / -78 - 20 °C / Inert atmosphere

9.2: 20 °C / Inert atmosphere

10.1: bis-triphenylphosphine-palladium(II) chloride; diethylamine; copper(l) iodide / 13 h / 0 - 20 °C / Inert atmosphere

11.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 72 h / Inert atmosphere

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 168 h / 55 °C / Inert atmosphere

13.1: pyridine / 24 h / 0 - 4 °C / Inert atmosphere

14.1: dimethyl sulfoxide / 2 h / 90 °C / Inert atmosphere

15.1: diisobutylaluminium hydride / dichloromethane / 3 h / -15 - 0 °C / Inert atmosphere

15.2: 2 h / 5 °C / Inert atmosphere

15.3: 2 h / -78 °C / Inert atmosphere

16.1: pyridine / 0 - 4 °C / Inert atmosphere

17.1: dimethyl sulfoxide / 90 °C / Inert atmosphere

18.1: diisobutylaluminium hydride / dichloromethane / 3 h / -15 - 0 °C / Inert atmosphere

18.2: 2 h / 5 °C / Inert atmosphere

18.3: 2 h / -78 °C / Inert atmosphere

19.1: 1H-imidazole / N,N-dimethyl-formamide / 10 h / 0 - 20 °C / Inert atmosphere

20.1: dipyridinium dichromate / dichloromethane / 20 °C / Inert atmosphere

21.1: potassium tert-butylate / tetrahydrofuran; toluene / -17 °C / Inert atmosphere

21.2: -17 - 20 °C / Inert atmosphere; Sonication

22.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; tricyclohexylphosphine; potassium acetate / dimethyl sulfoxide / 80 °C / Inert atmosphere

23.1: bis-triphenylphosphine-palladium(II) chloride; potassium phosphate / tetrahydrofuran / Inert atmosphere

24.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere; Darkness

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; copper(l) iodide; dipyridinium dichromate; n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; naphthalene; palladium 10% on activated carbon; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; potassium acetate; sodium; diisobutylaluminium hydride; diethylamine; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; tricyclohexylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; 21.1: |Wittig Olefination / 21.2: |Wittig Olefination / 22.1: |Miyaura Borylation Reaction / 23.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/jm3008272

upstream raw materials:

8β,22-bis(tert-butyldimethylsilyloxy)-de-A,B-23,24-dinorcholan-12-one

8β,22-bis(tert-butyldimethylsilyloxy)-de-A,B-23,24-dinorchol-11-en-12-yl trifluoromethanesulfonate

8β,22-bis(tert-butyldimethylsilyloxy)-12-(7-hydroxy-7-methyloct-1-ynyl)-de-A,B-23,24-dinorchol-11-ene

8β,22-bis(tert-butyldimethylsilyloxy)-12β-(7-hydroxy-7-methyloctyl)-de-A,B-23,24-dinorcholane

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