121651-93-2

Upstream product

• 625-72-9 (R)-3-hydroxybutyric acid 
• 2393-23-9 4-methoxy-benzylamine 
• 2975-46-4 3-(trimethylsilyl)prop-2-yn-1-al 
• 97363-14-9 (R)-3-hydroxybutyrate thiophenyl ester 
• 108053-19-6 (4-Methoxy-benzyl)-[3-trimethylsilanyl-prop-2-yn-(Z)-ylidene]-amine 

Downstream Products

• 111408-23-2 (3S,4S)-4-Ethynyl-3-<(1R)-hydroxyethyl>-2-azetidinone 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 105662-87-1 (3S,4S)-4-Ethynyl-3-<(1R)-hydroxyethyl>-N-p-methoxybenzyl-2-azetidinone 
• 125829-49-4 (3S,4S)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-4-trimethylsilanylethynyl-azetidin-2-one 
• 105620-49-3 (3R,4R)-4-Ethynyl-3-((S)-1-hydroxy-ethyl)-1-(4-methoxy-benzyl)-azetidin-2-one 
• 98729-69-2 (3S,4S)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-4-phenylsulfanylethynyl-azetidin-2-one 

Relevant academic research and scientific papers

NEW SYNTHESIS OF 4-ACETOXY-2-AZETIDINONES BY USE OF ELECTROCHEMICAL OXIDATION

4-Acetoxy-2-azetidinone was synthesized from 4-carboxy-2-azetidinone by Kolbe-type electrolysis.Optically pure 4-acetoxy-3--2-azetidinone, which is an important intermediate for the synthesis of thienamycin, and (+)-PS-5 were synthesized by use of this method.

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.