75767-11-2

Upstream product

• 67315-35-9 (Z)-2-((2S,3S)-3-Azido-2-methanesulfonyloxymethyl-4-oxo-azetidin-1-yl)-3-hydroxy-but-2-enoic acid benzyl ester 
• 75748-42-4 (2R,3S)-2-((2S,3S)-3-Azido-2-methanesulfonyloxymethyl-4-oxo-azetidin-1-yl)-3-(tert-butyl-dimethyl-silanyloxy)-butyric acid benzyl ester 
• 163234-32-0 benzyl 3-methyl-2-iso-oxacephem-4-carboxylate 
• 75748-43-5 (2R,3S)-2-((2S,3S)-3-Azido-2-hydroxymethyl-4-oxo-azetidin-1-yl)-3-(tert-butyl-dimethyl-silanyloxy)-butyric acid benzyl ester 
• 75748-41-3 (2R,3S)-2-((2S,3S)-3-Azido-2-methanesulfonyloxymethyl-4-oxo-azetidin-1-yl)-3-hydroxy-butyric acid benzyl ester 
• 75748-36-6 (2R,3S)-2-Amino-3-hydroxy-butyric acid benzyl ester; hydrochloride 
• 75748-38-8 (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-butyric acid benzyl ester 
• 75748-37-7 (2R,3S)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-butyric acid benzyl ester 
• 143061-91-0 (2R,3S)-2-[(3S,4R)-3-Azido-2-oxo-4-((E)-styryl)-azetidin-1-yl]-3-(tert-butyl-dimethyl-silanyloxy)-butyric acid benzyl ester 
• 75767-10-1 (6S,7S)-7-Azido-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester 

Downstream Products

• 75767-12-3 (6S,7S)-3-Methyl-8-oxo-7-phenylacetylamino-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester 
• 75767-13-4 (+)-3-methyl-7-phenyl-acetamido-O-2-isocephem 
• 62282-25-1 benzyl 7-β-(aminophenoxyacetoyl)-3-methyl-Δ³-O-2-isocephem-4-carboxylate 
• 62283-10-7 (6S,7S)-3-Methyl-8-oxo-7-phenylacetylamino-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester 
• 62283-14-1 (6S,7S)-7-(2-Benzyloxycarbonyl-2-phenyl-acetylamino)-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester 
• 62282-30-8 (6S,7S)-7-(2-Benzyloxycarbonylamino-2-phenyl-acetylamino)-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester 
• 62402-75-9 (6S,7S)-7-(2-Amino-2-phenyl-acetylamino)-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; hydrochloride 
• 62282-26-2 3-methyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 69809-99-0 7c-methoxy-3-methyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 69809-97-8 7c-methoxy-3-methyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester 
• 69809-95-6 3-methyl-7c-methylsulfanyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester 
• 69809-90-1 3-methyl-7c-methylsulfanyl-7t-(4-nitro-benzylideneamino)-8-oxo-(6rH)-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester 
• 69809-93-4 7t-amino-3-methyl-7c-methylsulfanyl-8-oxo-(6rH)-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Simple and Condensed &β-Lactams, XIX. - Synthesis of Some New 7-Acylamino-2-iso-oxacephem-4-carboxylic Acids

General methods have been developed for the synthesis of 7-amino-2-iso-oxacephem-4-carboxylic acid esters 21a, b; 35b.Clayfen was used for the preparation of benzyl 2,3-dioxobutyrate (3).The latter readily reacted with N(1)-unsubstituted β-lactams (9a, 28) to give products formed by addition reaction on the middle carbonyl-C atom.These intermediates furnished the corresponding acetoacetic esters 10, 29 which gave by ring closure the O-mono- and the O,N-diprotected-2-iso-oxacephems (11, 30).Intermolecular carbene insertion was used for the synthesis of tert-butyl 2-(2-oxoazetidin-1-yl)acetoacetates 19a, b whose ring closure led to the tert-butyl 2-iso-oxacephem-4-carboxylates 20a, b.The O-protecting tert-butyl group could be removed without decomposition of the 2-isooxacephem moiety to give 2-iso-oxacephem-4-carboxylic acids 2a, b which exhibit antibacterial activity against Grampositive microorganisms. - Key Words: Benzyl 2,3-dioxobutyrate / 2-Iso-oxacephems / Antibacterial activity