146963-17-9

Basic information

• Product Name: Methyl (E)-3-dimethyl(4-methylphenyl)silylprop-2-enoate
• Synonyms: Methyl (E)-3-dimethyl(4-methylphenyl)silylprop-2-enoate
• CAS NO: 146963-17-9
• Molecular Weight: 234.37
• Mol File: 146963-17-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Methyl (E)-3-dimethyl(4-methylphenyl)silylprop-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl (E)-3-dimethyl(4-methylphenyl)silylprop-2-enoate(146963-17-9)
• EPA Substance Registry System: Methyl (E)-3-dimethyl(4-methylphenyl)silylprop-2-enoate(146963-17-9)

Safety Data

• Hazardous Substances Data: 146963-17-9(Hazardous Substances Data)

Upstream product

• 106-38-7 para-bromotoluene 
• 1432-39-9 dimethyl-p-tolylsilane 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 146963-25-9 (3RS,4SR)-3,4-Biscyclopentan-1-one 
• 146963-21-5 Dimethyl (3RS,4SR)-3,4-bishexane-1,6-dioate 

Relevant articles and documents

Stereocontrol in organic synthesis using silicon-containing compounds. Syntheses of (±)-2-deoxyribonolactone and (±)-arabonolactone

Samarium iodide reacts with methyl (Z)-3-dimethyl(4-methylphenyl)silylprop-2-enoate 5b to give dimethyl (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]hexane-1,6-dioate 8b with high stereoselectivity. This meso diester can be converted into (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]pentan-5-olide 16 by Dieckmann cyclisation, demethoxycarbonylation and Baeyer-Villiger reaction. Silyl-to-hydroxy conversion and relactonisation gave (±)-deoxyribonolactone, and anti-selective enolate hydroxylation followed by silyl-to-hydroxy conversion gave (±)-arabonolactone. An attempt to synthesise sugars with the relative configuration (3RS,4RS) was thwarted by an unprecedented retention of configuration at the migration origin in the cationic rearrangement of (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]-5-hydroxypentanoic acid 28 to (3RS,4SR)-3,5-bis[dimethyl(4-methylphenyl)silyl]pentan-1,4-olide 30.