98729-69-2

Upstream product

• 125829-49-4 (3S,4S)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-4-trimethylsilanylethynyl-azetidin-2-one 
• 882-33-7 diphenyldisulfane 
• 103841-76-5 (2R,3R)-3-Methyl-oxirane-2-carboxylic acid (4-methoxy-benzyl)-(3-phenylsulfanyl-prop-2-ynyl)-amide 
• 931-59-9 benzenesulfenyl chloride 
• 98729-68-1 (2S,3R)-2-Bromo-3-hydroxy-N-(4-methoxy-benzyl)-N-(3-phenylsulfanyl-prop-2-ynyl)-butyramide 
• 98729-73-8 (4-Methoxy-benzyl)-(3-phenylsulfanyl-prop-2-ynyl)-amine 
• 70601-38-6 phenylthiopropargyl chloride 
• 108053-20-9 (2S,3S)-2-((R)-1-Hydroxy-ethyl)-3-(4-methoxy-benzylamino)-5-trimethylsilanyl-pent-4-ynethioic acid S-phenyl ester 

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.

CYCLIZATION REACTION OF N-PROPARGYL EPOXYAMIDE TO ACETYLENIC 2-AZETIDINONE, A PRECURSOR TO THIENAMYCIN AND RELATED CARBAPENEMS

Base treatment of N-propargyl epoxyamide 5 afforded the acetylenic 3-(hydroxyethyl)-2-azetidinone 9a, which was subsequently transformed to phenyl thiolester 2, a versatile intermediate for the carbapenem synthesis.