(10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-6-(1,3-dioxolan-2-yl)undec-1-ene

Base Information

• Chemical Name: (10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-6-(1,3-dioxolan-2-yl)undec-1-ene
• CAS No.: 1392104-09-4
• Molecular Formula: C₃₅H₅₆O₄Si₂
• Molecular Weight: 596.998
• Mol file: 1392104-09-4.mol

Synonyms:(10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-6-(1,3-dioxolan-2-yl)undec-1-ene

Chemical Property of (10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-6-(1,3-dioxolan-2-yl)undec-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-6-(1,3-dioxolan-2-yl)undec-1-ene

There total 4 articles about (10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-6-(1,3-dioxolan-2-yl)undec-1-ene 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: 86.0%

(10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-1-en-6-one (1392104-07-2) + ethylene glycol (107-21-1) → (10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-6-(1,3-dioxolan-2-yl)undec-1-ene (1392104-09-4)

Guidance literature:

With bismuth(lll) trifluoromethanesulfonate; orthoformic acid triethyl ester; In toluene; at 20 ℃;

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)-6-(1,3-dioxolan-2-yl)undec-1-ene (1392104-09-4)

Guidance literature:

Multi-step reaction with 3 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

3.1: bismuth(lll) trifluoromethanesulfonate; orthoformic acid triethyl ester / toluene / 20 °C

With bismuth(lll) trifluoromethanesulfonate; 1H-imidazole; dmap; iodine; magnesium; orthoformic acid triethyl ester; In diethyl ether; dichloromethane; toluene;

DOI:10.1039/c2ob06802h

Reference yield:

(5S)-5-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-N-methoxy-N-methylhexanamide (1392104-08-3) → (10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-6-(1,3-dioxolan-2-yl)undec-1-ene (1392104-09-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: iodine; magnesium / diethyl ether / Inert atmosphere

1.2: 3 h / 0 °C / Inert atmosphere

2.1: bismuth(lll) trifluoromethanesulfonate; orthoformic acid triethyl ester / toluene / 20 °C

With bismuth(lll) trifluoromethanesulfonate; iodine; magnesium; orthoformic acid triethyl ester; In diethyl ether; 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

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

ethylene glycol

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