(E,Z)-1-Methoxy-2-methyl-3- (trimethylsilyloxy)-1,3-pentadiene Chemical Properties

Boiling point:

65 °C/6 mmHg (lit.)

Density 

0.899 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.4650(lit.)

Flash point:

178 °F

storage temp. 

2-8°C

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

(E,Z)-1-Methoxy-2-methyl-3- (trimethylsilyloxy)-1,3-pentadiene Usage And Synthesis

Uses

Danishefsky diene used as a reactant for:
Preparation of migrastatin analog as cell migration inhibitor for treatment of tumor metastasis
Preparation of dihydropyridinones by chlorosilane-promoted aza-Diels-Alder addition
Synthesis on non-proteinogenic amino esters via stereoselective Lewis acid-catalyzed aza-Diels-Alder cycloaddition with conjugated (cyclo)dienes

Uses

(1E,3Z)-1-Methoxy-2-methyl-3-(trimethylsilyloxy)-1,3-pentadiene used as a reactant for:Preparation of migrastatin analog as cell migration inhibitor for treatment of tumor metastasis2Preparation of dihydropyridinones by chlorosilane-promoted aza-Diels-Alder addition3Synthesis on non-proteinogenic amino esters via stereoselective Lewis acid-catalyzed aza-Diels-Alder cycloaddition with conjugated (cyclo)dienes4

Synthesis

(1E,3Z)-1-Methoxy-2-Methyl-3-(triMethylsilyloxy)-1,3-pentadiene is prepared in multigram quantities as a colorless or slightly yellow liquid from 3- pentanone and ethyl formate via a three-step procedure (ca. 40% overall yield).