(10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-1-en-6-one

Base Information

• Chemical Name: (10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-1-en-6-one
• CAS No.: 1392104-07-2
• Molecular Formula: C₃₃H₅₂O₃Si₂
• Molecular Weight: 552.945
• Mol file: 1392104-07-2.mol

Synonyms:(10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-1-en-6-one

Chemical Property of (10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-1-en-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-1-en-6-one

There total 3 articles about (10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-1-en-6-one 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: 79.0%

(5S)-5-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-N-methoxy-N-methylhexanamide (1392104-08-3) + bromopentene (1119-51-3) → (10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-1-en-6-one (1392104-07-2)

Guidance literature:

bromopentene; With iodine; magnesium; In diethyl ether; Inert atmosphere;

(5S)-5-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-N-methoxy-N-methylhexanamide; In diethyl ether; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c2ob06802h

Reference yield:

6-(tert-butyldiphenylsilyloxy)-(5S)-5-hydroxyl-N-methoxy-N-methylhexanamide (1392104-16-3) → (10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-1-en-6-one (1392104-07-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1H-imidazole; dmap / dichloromethane / 13 h / 20 - 45 °C / Inert atmosphere

2.1: iodine; magnesium / diethyl ether / Inert atmosphere

2.2: 3 h / 0 °C / Inert atmosphere

With 1H-imidazole; dmap; iodine; magnesium; In diethyl ether; dichloromethane;

DOI:10.1039/c2ob06802h

Reference yield:

(S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxyhexanoic acid δ-lactone (175398-31-9) → (10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-1-en-6-one (1392104-07-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trimethylaluminum / dichloromethane; toluene / 0 °C

1.2: 0 - 20 °C

2.1: 1H-imidazole; dmap / dichloromethane / 13 h / 20 - 45 °C / Inert atmosphere

3.1: iodine; magnesium / diethyl ether / Inert atmosphere

3.2: 3 h / 0 °C / Inert atmosphere

With 1H-imidazole; dmap; iodine; trimethylaluminum; magnesium; In diethyl ether; dichloromethane; toluene;

DOI:10.1039/c2ob06802h

upstream raw materials:

6-(tert-butyldiphenylsilyloxy)-(5S)-5-hydroxyl-N-methoxy-N-methylhexanamide

(5S)-5-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-N-methoxy-N-methylhexanamide

bromopentene

(S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxyhexanoic acid δ-lactone

Downstream raw materials:

8-ethynyl-2-(tert-butyldiphenylsilyloxymethyl)-1,7-dioxaspiro[5.5]undecane

14-(4-(8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1H-1,2,3-triazol-1-yl)tetradecane-2,5-dione

11-(4-(8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1H-1,2,3-triazol-1-yl)undecan-2-one

1-(10-(tert-butyldimethylsilyloxy)decyl)-4-((2S,6S,8S)-8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1H-1,2,3-triazole