65338-32-1

Basic information

• Product Name: cefamandole
• Synonyms: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[(hydroxyphenylacetyl)amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, [6R-(6α,7β)]-
• CAS NO: 65338-32-1
• Molecular Formula: C₁₈H₁₈N₆O₅S₂
• Molecular Weight: 462.5
• Mol File: 65338-32-1.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: cefamandole(CAS DataBase Reference)
• NIST Chemistry Reference: cefamandole(65338-32-1)
• EPA Substance Registry System: cefamandole(65338-32-1)

Safety Data

• Hazardous Substances Data: 65338-32-1(Hazardous Substances Data)

Upstream product

• 20698-91-3 (R)-methyl mandelate 
• 24209-38-9 (6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid 
• 51818-85-0 7-[(1-hydroxy-1-phenyl)-acetamido]-3-acetoxymethyl-Δ³-cephem-4-carboxylic acid 
• 13183-79-4 1-methyl-5-mercaptotetrazole 
• 42540-40-9 cefamandole nafate 

Downstream Products

• 58333-59-8 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetoxymethyl ester 
• 57268-80-1 Cefamandole nafate 
• 42540-40-9 cefamandole nafate 
• 70579-78-1 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-tert-butoxycarbonyl-L-isoleucyloxymethyl ester 
• 70579-79-2 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (N-tert-butoxycarbonyl-L-phenylalanyloxy)-methyl ester 
• 70579-75-8 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-tert-butoxycarbonyl-glycyloxymethyl ester 
• 70606-86-9 N-tert-butoxycarbonyl-L-aspartic acid 4-[(6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carbonyloxymethyl] ester 1-methyl ester 
• 70579-77-0 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-tert-butoxycarbonyl-L-leucyloxymethyl ester 
• 70579-76-9 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-tert-butoxycarbonyl-L-valyloxymethyl ester 

Relevant articles and documents

Formylation of glucose by cefamandole nafate at alkaline pH

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PROCESS FOR THE FORMYLATION OF CEFAMANDOLE

The present invention relates to a process for the preparation of O-formyl cefamandole, an intermediate in the preparation of cefamandole nafate, by formylation of cefamandole.

Influence of substrate structure on PGA-catalyzed acylations. Evaluation of different approaches for the enzymatic synthesis of cefonicid

The influence of the substrate structure on the catalytic properties of penicillin G acylase (PGA) from Escherichia coli in kinetically controlled acylations has been studied. In particular, the affinity of different β-lactam nuclei towards the active site has been evaluated considering the ratio between the rate of synthesis (vs) and the rate of hydrolysis of the acylating ester (vhl). 7-Aminocephalosporanic acid (7-ACA) and 7-amino-3-(1-sulfomethyl-1,2,3,4-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (7-SACA) showed a good affinity for the active centre of PGA. The enzymatic acylation of these nuclei with R-methyl mandelate has been studied in order to evaluate different approaches for the enzymatic synthesis of cefonicid. The best results have been obtained in the acylation of 7-SACA. Cefonicid (8) was recovered from the reaction mixture as the disodium salt in 65% yield and about 95% of purity. Furthermore, through acylation of 7-ACA, a "one-pot" chemo-enzymatic synthesis was carried out starting from cephalosporin C using three enzymes in sequence: D-amino acid oxidase (DAO), glutaryl acylase (GA) and PGA. Cefonicid disodium salt was obtained in three steps, avoiding any intermediate purification, in 35% overall yield and about 94% purity. This approach presents several advantages compared with the classical chemical processes.