66260-72-8

Upstream product

• 73395-53-6 N-[2-(Benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide 
• 108-59-8 malonic acid dimethyl ester 
• 75283-03-3 2-[2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-2-enoic acid methyl ester 

Downstream Products

• 95477-41-1 7-Oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2,3,3-tricarboxylic acid dimethyl ester 4-nitro-benzyl ester 
• 95477-38-6 2-[1-[Chloro-(4-nitro-benzyloxycarbonyl)-methyl]-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-2-ylsulfanyl]-malonic acid dimethyl ester 
• 95477-44-4 7-Oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2,3,3-tricarboxylic acid dimethyl ester 
• 95477-35-3 2-[1-[Hydroxy-(4-nitro-benzyloxycarbonyl)-methyl]-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-2-ylsulfanyl]-malonic acid dimethyl ester 
• 66260-73-9 (5R)-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2ξ,3,3-tricarboxylic acid 2-tert-butyl ester 3,3-dimethyl ester 

Relevant academic research and scientific papers

Carbon nucleophilic displacements on Kamiya's azetidinone disulfide: Synthesis of C-2 modified penicillins

Novel carbon nucleophilic displacement reactions on Kamiya's azetidinone disulfide 2 and the synthesis of the C-2 modified penams 25, 26 and 27 from the intermediates 8, 9, and 11 are described.

Syntheses based on 1,2-secopenicillins. Part 5. Penicillin analogues with electron-withdrawing 2-substituents

6-Acylaminopenam-3-carboxylic esters substituted at C-2 by one or two alkoxycarbonyl groups or by an acetyl group have been prepared from penicillins. The azetidinone ring remained intact throughout the reaction sequence, and the thiazolidine ring was completed by intramolecular alkylation at an activated methylene or methine group adjacent to the sulphur atom. Only in the case of the 2-alkoxycarbonylpenams could stable carboxylic acids be liberated from the esters.