(20S)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]vitamin D₃ tert-butyl dimethylsilyl ether

Base Information

• Chemical Name: (20S)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]vitamin D₃ tert-butyl dimethylsilyl ether
• CAS No.: 1451070-71-5
• Molecular Formula: C₄₆H₈₆O₃Si₃
• Molecular Weight: 771.444

Synonyms:(20S)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]vitamin D₃ tert-butyl dimethylsilyl ether

Chemical Property of (20S)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]vitamin D₃ tert-butyl dimethylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (20S)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]vitamin D₃ tert-butyl dimethylsilyl ether

There total 28 articles about (20S)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]vitamin D₃ tert-butyl dimethylsilyl 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: 70.0%

C46H86O3Si3 → (20S)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]vitamin D3 tert-butyl dimethylsilyl ether (1451070-71-5)

Guidance literature:

In hexane; at 60 ℃; for 19h; Inert atmosphere;

Reference yield:

(1R,3R,5R)-1-acetoxy-3-[(tert-butyldimethylsilyl)oxy]-4-methylene-6-oxabicyclo[3.2.1]octan-7-one → (20S)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]vitamin D3 tert-butyl dimethylsilyl ether (1451070-71-5)

Guidance literature:

Multi-step reaction with 11 steps

1: methanol / 17 h / 20 °C / Inert atmosphere

2: 2,6-dimethylpyridine / dichloromethane / 1 h / -40 °C

3: Martins sulfurane / tetrachloromethane / 0.5 h / 20 °C / Inert atmosphere

4: diethyl ether / 2 h / 20 °C / Darkness

5: dimethyl sulfoxide / 32 h / 125 °C / Inert atmosphere

6: diisobutylaluminium hydride / toluene; dichloromethane / 2 h / -78 °C / Inert atmosphere

7: dipyridinium dichromate / dichloromethane / 4 h / 20 °C

8: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

9: copper(l) iodide; bis(acetato)bis(triphenylphosphine)palladium⁽⁰⁾; diethylamine / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

10: quinoline; hydrogen / hexane / 0.75 h / 20 °C

11: hexane / 19 h / 60 °C / Inert atmosphere

With 2,6-dimethylpyridine; quinoline; methanol; copper(l) iodide; dipyridinium dichromate; n-butyllithium; bis(acetato)bis(triphenylphosphine)palladium⁽⁰⁾; Martins sulfurane; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; diethylamine; In tetrahydrofuran; tetrachloromethane; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

(1R,3R,5R)-1-acetoxy-3-[(tert-butyldimethylsilyl)oxy]-6-oxa-bicyclo[3.2.1]octane-4,7-dione (766529-88-8) → (20S)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]vitamin D3 tert-butyl dimethylsilyl ether (1451070-71-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / 0 - 20 °C

1.2: 1 h / 20 °C

2.1: methanol / 17 h / 20 °C / Inert atmosphere

3.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -40 °C

4.1: Martins sulfurane / tetrachloromethane / 0.5 h / 20 °C / Inert atmosphere

5.1: diethyl ether / 2 h / 20 °C / Darkness

6.1: dimethyl sulfoxide / 32 h / 125 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / toluene; dichloromethane / 2 h / -78 °C / Inert atmosphere

8.1: dipyridinium dichromate / dichloromethane / 4 h / 20 °C

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

10.1: copper(l) iodide; bis(acetato)bis(triphenylphosphine)palladium⁽⁰⁾; diethylamine / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

11.1: quinoline; hydrogen / hexane / 0.75 h / 20 °C

12.1: hexane / 19 h / 60 °C / Inert atmosphere

With 2,6-dimethylpyridine; quinoline; methanol; copper(l) iodide; dipyridinium dichromate; n-butyllithium; bis(acetato)bis(triphenylphosphine)palladium⁽⁰⁾; Martins sulfurane; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; diethylamine; In tetrahydrofuran; tetrachloromethane; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination;

upstream raw materials:

(1R,3R,5R)-1-acetoxy-3-[(tert-butyldimethylsilyl)oxy]-6-oxa-bicyclo[3.2.1]octane-4,7-dione

(3R,5R)-5-[(tert-butyldimethylsilyl)oxy]-1,3-dihydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

(20S)-1α,3β-bis[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-9,10-secocholesta-5(10),8-dien-6-yne

Downstream raw materials:

(20S)-1α,25-dihydroxy-2-methylene vitamin D₃

(5E)-(20S)-1α,25-dihydroxy-2-methylene vitamin D₃

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