109151-02-2

Upstream product

• 109151-01-1 (3R,4S)-3-Ethyl-1-((R)-1-phenyl-ethyl)-4-trimethylsilanylethynyl-azetidin-2-one 
• 882-33-7 diphenyldisulfane 
• 109151-01-1 (3R,4S)-3-Ethyl-1-((S)-1-phenyl-ethyl)-4-trimethylsilanylethynyl-azetidin-2-one 
• 146987-87-3 ((S)-1-Phenyl-ethyl)-[3-trimethylsilanyl-prop-2-yn-(E)-ylidene]-amine 
• 109150-99-4 (2S,3R)-2-Ethyl-3-((S)-1-phenyl-ethylamino)-5-trimethylsilanyl-pent-4-ynethioic acid S-phenyl ester 

Downstream Products

• 109151-04-4 (2R,3R)-3-ethyl-4-oxo-1-<(S)-1-phenylethyl>azetidine-2-ethanol 
• 109151-05-5 (3R,4R)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-ethyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one 
• 109151-03-3 (3R,4R)-4-ethenyl-3-ethyl-1-<(S)-1-phenylethyl>-2-azetidinone 

Relevant academic research and scientific papers

A method for the synthesis of alkynyl phenyl sulfides from alkynyltrimethylsilanes. A novel, efficient synthesis of the thienamycin intermediate from 3(R)-hydroxybutyric acid

The mechanism of the one-pot conversion of β-amino thiol esters of type 3 to β-lactams of type 4 has been clarified, and it is proposed that the actual active species is a PhSSPh-CuOTf complex. Through the use of this novel reaction, an efficient synthesis of the thienamycin intermediate 2, starting with 3(R)-hydroxybutyric acid, has been achieved. Furthermore, the combined reagents (PhSSPh-CuOTf) have been demonstrated to be a powerful source of PhS+ through the conversion of several alkynyltrimethylsilanes to alkynyl phenyl sulfides.

Asymmetric Synthesis of the Carbapenem Antibiotic (+)-PS-5

An asymmetric synthesis of (+)-PS-5 (1) has been accomplished by a route utilizing the anti-selective boron enolate-imine condensation reaction with extremely high asymmetric induction.