1α,23-dihydroxy-12β-(7-hydroxy-7-methyloctyl)-24,25,26,27-tetranorvitamin D3

Base Information

Chemical Name:1α,23-dihydroxy-12β-(7-hydroxy-7-methyloctyl)-24,25,26,27-tetranorvitamin D3
CAS No.:1402432-36-3
Molecular Formula:C₃₂H₅₄O₄
Molecular Weight:502.778
Hs Code.:

Synonyms:

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Chemical Property of 1α,23-dihydroxy-12β-(7-hydroxy-7-methyloctyl)-24,25,26,27-tetranorvitamin D3

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Technology Process of 1α,23-dihydroxy-12β-(7-hydroxy-7-methyloctyl)-24,25,26,27-tetranorvitamin D3

There total 17 articles about 1α,23-dihydroxy-12β-(7-hydroxy-7-methyloctyl)-24,25,26,27-tetranorvitamin 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:

: 1402432-29-4
8β,22-bis(tert-butyldimethylsilyloxy)-12-(7-hydroxy-7-methyloct-1-ynyl)-de-A,B-23,24-dinorchol-11-ene

: 1402432-36-3
1α,23-dihydroxy-12β-(7-hydroxy-7-methyloctyl)-24,25,26,27-tetranorvitamin D3

Guidance literature:: Multi-step reaction with 11 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: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

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

8.1: potassium tert-butylate / tetrahydrofuran; toluene / 3 h / -17 °C / Inert atmosphere

8.2: 5 h / -17 - 20 °C / Inert atmosphere; Sonication

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

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

11.1: 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; 8.1: |Wittig Olefination / 8.2: |Wittig Olefination / 9.1: |Miyaura Borylation Reaction / 10.1: |Suzuki-Miyaura Coupling;
DOI:10.1021/jm3008272

Reference yield:

: 1402432-37-4
(E)-23-(tert-butyldimethylsilyloxy)-12β-(7-hydroxy-7-methyloctyl)-8-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene]-de-A,B-24-norcholane

: 1402432-36-3
1α,23-dihydroxy-12β-(7-hydroxy-7-methyloctyl)-24,25,26,27-tetranorvitamin D3

Guidance literature:: Multi-step reaction with 2 steps

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

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

With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; tetrabutyl ammonium fluoride; In tetrahydrofuran; 1: |Suzuki-Miyaura Coupling;
DOI:10.1021/jm3008272

Reference yield:

: 244278-94-2
(1R,3aR,7aR)-2,3,3a,4,7,7a-hexahydro-1-[(S)-2-[(1,1-dimethylethyl)dimethylsilyloxy]-1-methylethyl]-7a-methyl-4H-inden-4-one

: 1402432-36-3
1α,23-dihydroxy-12β-(7-hydroxy-7-methyloctyl)-24,25,26,27-tetranorvitamin D3

Guidance literature:: Multi-step reaction with 22 steps

1.1: diisobutylaluminium hydride / dichloromethane; tetrahydrofuran / 0.5 h / -78 - 20 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere; Darkness

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

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere; Darkness

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

6.2: 1 h / Inert atmosphere

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

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

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

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

10.2: 20 °C / Inert atmosphere

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

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

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

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

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

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

16.2: 2 h / 5 °C / Inert atmosphere

16.3: 2 h / -78 °C / Inert atmosphere

17.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

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

19.1: potassium tert-butylate / tetrahydrofuran; toluene / 3 h / -17 °C / Inert atmosphere

19.2: 5 h / -17 - 20 °C / Inert atmosphere; Sonication

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

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

22.1: 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; 19.1: |Wittig Olefination / 19.2: |Wittig Olefination / 20.1: |Miyaura Borylation Reaction / 21.1: |Suzuki-Miyaura Coupling;
DOI:10.1021/jm3008272