10209-11-7

Upstream product

• 62499-66-5 Desacetoxy-cephalosporin-V-2'-bromethylester 
• 28974-31-4 4-nitrobenzyl 7β-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate 
• 33465-48-4 (6R)-3-methyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester 
• 87-08-1 penicilin V 
• 65538-78-5 Penicillin-V-2'-bromethylester 
• 81199-19-1 allyl (6R,7R) 7-phenoxyacetamido-10-desacetoxyceph-3-em-4-carboxylate 
• 22252-43-3 3-deacetyloxy-7-aminocephalosporanic acid 
• 701-99-5 Phenoxyacetyl chloride 
• 81483-01-4 (6R,7R)-7-[tert-Butoxycarbonyl-(2-phenoxy-acetyl)-amino]-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 62499-63-2 Penicillin-V-sulfoxid-2'-bromethylester 
• 93780-35-9 (6R,7R)-3-Methyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-(4-nitro-phenoxy)-ethyl ester 

Downstream Products

• 28643-84-7 3-methyl-7β-phenoxyacetamido-3-cephem-4-carbonyl chloride 
• 71877-86-6 [(6R)-3-methyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-2-yl]-carbamic acid tert-butyl ester 
• 71877-85-5 [(6R)-3-methyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-en-2ξ-yl]-carbamic acid tert-butyl ester 
• 51415-85-1 (pivaloyloxy)methyl 3-methyl-7-(2-phenoxyacetamido)ceph-3-em-4-carboxylate 
• 54237-57-9 methoxymethyl-7-phenoxyacetylamino-8-oxo-3-methyl-5-thia-1-azabicyclo<4.0.2>oct-2-ene-2-carboxylate 
• 93780-35-9 (6R,7R)-3-Methyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-(4-nitro-phenoxy)-ethyl ester 
• 96244-43-8 7-(phenoxyacetamido)deacetoxycephalosporanic acid 1β-oxide 
• 81199-19-1 allyl (6R,7R) 7-phenoxyacetamido-10-desacetoxyceph-3-em-4-carboxylate 
• 10209-06-0 (6R,7R)-methyl 3-methyl-8-oxo-7-(2-phenoxyacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 124876-47-7 allyl (6R,7R) 7-phenoxyacetamido-1,1-dioxo-10-desacetoxyceph-3-em-4-carboxylate 
• 129253-79-8 allyl (6R,7R) 7-phenoxyacetamido-1,1-dioxo-2-methylene-10-desacetoxyceph-3-em-4-carboxylate 
• 300810-87-1 allyl (6R,7R) 7-phenoxyacetamido-1,1-dioxo-2-phenylselenomethyl-10-desacetoxyceph-3-em-4-carboxylate 
• 80903-76-0 (pivaloyloxy)methyl 1-hydroxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate 
• 84235-67-6 (pivaloyloxy)methyl 2-methyl-1-oxo-6-(2-phenoxyacetamido)carbapen-2-em-3-carboxylate 

Relevant academic research and scientific papers

Titanium tetrachloride promoted hydrolysis of cephalosporin tert-butyl esters

Titanium tetrachloride was used as a mild and effective deprotective reagent for the hydrolysis of cephalosporin tert-butyl esters. Yields up to 91% were obtained.

Novel Cephalosporins Selectively Active on Nonreplicating Mycobacterium tuberculosis

We report two series of novel cephalosporins that are bactericidal to Mycobacterium tuberculosis alone of the pathogens tested, which only kill M. tuberculosis when its replication is halted by conditions resembling those believed to pertain in the host, and whose bactericidal activity is not dependent upon or enhanced by clavulanate, a β-lactamase inhibitor. The two classes of cephalosporins bear an ester or alternatively an oxadiazole isostere at C-2 of the cephalosporin ring system, a position that is almost exclusively a carboxylic acid in clinically used agents in the class. Representatives of the series kill M. tuberculosis within macrophages without toxicity to the macrophages or other mammalian cells.

Design and synthesis of new cephalosporin antibiotics

Cephalosporins are important antibiotics. We synthesized new cephalosporin analogs containing novel side chains of methyl, propyl, benzyl, and phenoxy groups. Four synthetic methods with N-alkylation and N-acylation at position C-7 and esterification at position C-4 of 7-aminodesacetoxycephalosporanic acid are reported here. Graphical Abstract: [Figure not available: see fulltext.]

Reactions of cephalosporin sulfones 3. Synthesis of 2- phenylhydrazonocephem-sulfones. A new potential entry to 2-aminocephems [1]

Reaction of cephem sulfones 1a-e with aryldiazonium salts gives the 2-azo compounds which immediately rearrange into the corresponding 2-hydrazono derivatives 2a-e.

Radical rearrangement: A strategy for conversion of cephalosporin to 1-carba(dethia)cephalosporin

A radical rearrangement approach to semisynthesis of the carbacephem class of β-lactam antibiotics is reported. The crucial bond construction in assembly of the carbacephem framework was accomplished by intramolecular C-C bond formation between an azetidi

De-esterification process

An efficient process for de-esterification has been provided for by application of special tetrahalogenides. By applying this process a new compound, viz. cefesone, and especially the E-isomer thereof, has been prepared.

Extremely Selective and Mild Cleavage of β-Haloalkyl Groups by Cobalt(I)phthalocyanine Anion in Semisyntheses of β-Lactam Antibiotics

Cleavage of β-haloalkyl groups can be performed extremely selectively by cobalt(I)phthalocyanine anion under very mild conditions, qualifying it best in the chemistry of highly sensitive β-lactam antibiotics.This is demonstrated in penicillin and cephalosporin semisyntheses.

A New Dihydrothiazine Ring Closure for the Preparation of 3-Methylcephalosporins from Azetidinone Disulfides at 5-10 deg

p-Nitrobenzyl (2 R, 3 R)-2-(benzothiazol-2'-yldithio)-α-isopropenyl-4-oxo-3-phenoxyacetylamino-azetidine-1-acetate (3a), readily prepared from penicillin V, is smoothly cyclized by ammonium acetate in a dimethyl sulfoxide/tetrahydrofuran mixture at 5-10 deg to the ceph-3-em ester (2a) in high yield.Other ethers (3b-d), but not the free acid (3e), behave in a similar way.The ceph-3-em esters can be readily de-esterified to the free acid (2e).

AZETIDINONE IMIDES

The synthesis of acetyl and Boc azetidinone imides is described.