2-Pentenoic acid, 5-(((1,1-dimethylethyl)dimethylsilyl)oxy)-3-methyl-, (E)-

Base Information

• Chemical Name: 2-Pentenoic acid, 5-(((1,1-dimethylethyl)dimethylsilyl)oxy)-3-methyl-, (E)-
• CAS No.: 88968-96-1
• Molecular Formula: C₁₂H₂₄O₃Si
• Molecular Weight: 244.406
• Mol file: 88968-96-1.mol

Synonyms:2-Pentenoic acid, 5-(((1,1-dimethylethyl)dimethylsilyl)oxy)-3-methyl-, (E)-;88968-96-1;SCHEMBL3143186

Chemical Property of 2-Pentenoic acid, 5-(((1,1-dimethylethyl)dimethylsilyl)oxy)-3-methyl-, (E)-

Chemical Property:

• Vapor Pressure: 8.53E-05mmHg at 25°C
• Boiling Point: 316.8°Cat760mmHg
• Flash Point: 145.4°C
• Density: 0.951g/cm³
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 244.14947116
• Heavy Atom Count: 16
• Complexity: 275

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC(=O)O)CCO[Si](C)(C)C(C)(C)C
• Isomeric SMILES: C/C(=C\C(=O)O)/CCO[Si](C)(C)C(C)(C)C

Technology Process of 2-Pentenoic acid, 5-(((1,1-dimethylethyl)dimethylsilyl)oxy)-3-methyl-, (E)-

There total 6 articles about 2-Pentenoic acid, 5-(((1,1-dimethylethyl)dimethylsilyl)oxy)-3-methyl-, (E)- 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: 75.0%

carbon dioxide (124-38-9,18923-20-1) + (E)-4-tert-butyldimethylsilyloxy-1-iodo-2-methyl-1-butene (78592-77-5) → 5-((tert-Butyldimethylsilyl)oxy)-3-methyl-2(E)-pentenoic Acid (88968-96-1)

Guidance literature:

With n-butyllithium; In diethyl ether; 1) Et₂O, -60 deg C 2) -78 deg C;

DOI:10.1021/jo00184a021

Reference yield: 59.0%

2,2,2-Trichloroethyl 5-Hydroxy-3-methyl-2(E)-pentenoate (88968-95-0) → 5-((tert-Butyldimethylsilyl)oxy)-3-methyl-2(E)-pentenoic Acid (88968-96-1)

Guidance literature:

With 1H-imidazole; potassium dihydrogenphosphate; tert-butyldimethylsilyl chloride; zinc; 1) DMF, 2) THF;

DOI:10.1021/jo00153a035

Reference yield:

2,2,2-Trichloroethyl-5-(tert-butyltrimethylsilyloxy)-3-methyl-2(E)-pentenoate → 5-((tert-Butyldimethylsilyl)oxy)-3-methyl-2(E)-pentenoic Acid (88968-96-1)

Guidance literature:

With potassium dihydrogenphosphate; zinc; In tetrahydrofuran; at 25 ℃; for 16h; Yield given;

DOI:10.1021/jo00184a021

upstream raw materials:

mevalonolactone

carbon dioxide

(E)-4-tert-butyldimethylsilyloxy-1-iodo-2-methyl-1-butene

2,2,2-Trichloroethyl 5-Hydroxy-3-methyl-2(E)-pentenoate

Downstream raw materials:

12,13-Epoxytrichothec-9-ene-4β,15-diol 15-<5'-<(1,1-Dimethylethyl)dimethylsilyloxy>-3'-methyl-2'(E)-pentenoate>

12,13-Epoxytrichothec-9-ene-4β,15-diol 15-<5'-<(1,1-Dimethylethyl)dimethylsilyloxy>-3'-methyl-2'(E)-pentenoate>

C₂₉H₃₈O₉

12,13-Epoxytrichothec-9-ene-4β,15-diol 15-(5'-Hydroxy-3'-methyl-2'(Z)-pentenoate)