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

Base Information

• Chemical Name: 1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]vitamin D₃ tert-butyl dimethylsilyl ether
• CAS No.: 1451070-70-4
• Molecular Formula: C₄₆H₈₆O₃Si₃
• Molecular Weight: 771.444

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

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

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 25 articles about 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: 100.0%

C46H86O3Si3 → 1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]vitamin D3 tert-butyl dimethylsilyl ether (1451070-70-4)

Guidance literature:

In hexane; at 60 ℃; for 14h; Inert atmosphere;

Reference yield:

[(3’R,5’R)-3’,5’-bis[(tert-butyldimethylsilyl)oxy]-2’-methyl-4’-methylene-cyclohex-1’-enyl]methanol → 1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]vitamin D3 tert-butyl dimethylsilyl ether (1451070-70-4)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: copper(l) iodide; diethylamine; Pd(PPh₃)(OAc)2 / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

4: hydrogen / hexane; quinoline / 2.5 h / 20 °C

5: hexane / 14 h / Inert atmosphere; Heating

With copper(l) iodide; dipyridinium dichromate; n-butyllithium; Pd(PPh₃)(OAc)2; hydrogen; diethylamine; In tetrahydrofuran; quinoline; hexane; dichloromethane; N,N-dimethyl-formamide; 3: |Sonogashira Cross-Coupling;

DOI:10.1021/acs.jmedchem.5b01295

Reference yield:

(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-4-methylene-cyclohex-1-enecarbaldehyde (1428946-46-6) → 1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]vitamin D3 tert-butyl dimethylsilyl ether (1451070-70-4)

Guidance literature:

Multi-step reaction with 4 steps

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

2: copper(l) iodide; diethylamine; Pd(PPh₃)(OAc)2 / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

3: hydrogen / hexane; quinoline / 2.5 h / 20 °C

4: hexane / 14 h / Inert atmosphere; Heating

With copper(l) iodide; n-butyllithium; Pd(PPh₃)(OAc)2; hydrogen; diethylamine; In tetrahydrofuran; quinoline; hexane; N,N-dimethyl-formamide; 2: |Sonogashira Cross-Coupling;

DOI:10.1021/acs.jmedchem.5b01295

upstream raw materials:

Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate

Downstream raw materials:

1α,25-dihydroxy-2-methylene-vitamin D₃

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