140869-82-5

Basic information

• Product Name: 1-(4-methoxyphenyl)-3-(1-methylethyl)-4-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>azetidin-2-one
• CAS NO: 140869-82-5
• Molecular Weight: 377.599
• Mol File: 140869-82-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-(4-methoxyphenyl)-3-(1-methylethyl)-4-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-methoxyphenyl)-3-(1-methylethyl)-4-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>azetidin-2-one(140869-82-5)
• EPA Substance Registry System: 1-(4-methoxyphenyl)-3-(1-methylethyl)-4-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>azetidin-2-one(140869-82-5)

Safety Data

• Hazardous Substances Data: 140869-82-5(Hazardous Substances Data)

Upstream product

• 104-94-9 4-methoxy-aniline 
• 139007-44-6 S-(2-pyridinyl) 3-methylbutanethioate 
• 135508-31-5 (2S)-2-(t-butyl-dimethylsilyloxy)-N-(p-methoxyphenyl)-propanal imine 
• 141781-21-7 [(S)-2-(tert-Butyl-dimethyl-silanyloxy)-prop-(E)-ylidene]-(4-methoxy-phenyl)-amine 
• 87727-28-4 (S)-2-tert-butyl-dimethyl-silanyloxy propanal 

Relevant articles and documents

Synthesis of β-lactams by condensation of titanium enolates of 2-pyridylthioesters with imines. Influence of the imine structure on the trans/cis stereoselectivity

The condensation of the titanium enolates of C-2 alkyl substituted 2-pyridylthioesters with imines affords β-lactams in trans/cis ratios that largely depend on the structure of the C-imine residue. Bulky and non-chelating heteroatom-containing groups lead to the formation of trans β-lactams, while sterically non-requiring or chelating groups favour the formation of the cis-products. On the basis of NMR evidences a rationale is proposed to account for the observed stereoselectivity.

Highly diastereoselective synthesis of β-lactams by addition of titanium enolates of 2-pyridyl thioesters to chiral imines

Addition of titanium enolates of 2-pyridyl thioesters to chiral imines derived from alkoxy aldehydes occurs with good diastereofacial control, and opens a simple access to important carbapenem antibiotics.