cefamandole

Base Information

• Chemical Name: cefamandole
• CAS No.: 144125-09-7
• Molecular Formula: C₁₈H₁₈N₆O₅S₂
• Molecular Weight: 462.51
• Mol file: 144125-09-7.mol

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(S*)]]-

Chemical Property of cefamandole

Chemical Property:

• PSA: 201.14000
• LogP: 0.10320

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)-Cefamandole is a stereoisomer of Cefamandole (C440145), a second-generation cephalosporin antibiotic with antibacterial activity.

Technology Process of cefamandole

There total 6 articles about cefamandole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

7-[(1-hydroxy-1-phenyl)-acetamido]-3-acetoxymethyl-Δ3-cephem-4-carboxylic acid (51818-85-0) + 1-methyl-5-mercaptotetrazole (13183-79-4) → cefamandole (65338-32-1,144125-09-7,34444-01-4)

Guidance literature:

In water; at 65 ℃;

DOI:10.1016/S0960-894X(01)00463-2

Reference yield:

(R)-methyl mandelate (20698-91-3) + (6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid (24209-38-9) → cefamandole (65338-32-1,144125-09-7,34444-01-4)

Guidance literature:

With 3G₃K penicillin G acylase immobilized on glyoxyl agarose; at 4 ℃; pH=6.5; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1002/ejoc.200801204

Reference yield:

cefamandole nafate (42540-40-9) → cefamandole (65338-32-1,144125-09-7,34444-01-4)

Guidance literature:

With sodium carbonate;

DOI:10.1002/jps.2600650811

upstream raw materials:

cefamandole nafate

7-[(1-hydroxy-1-phenyl)-acetamido]-3-acetoxymethyl-Δ³-cephem-4-carboxylic acid

1-methyl-5-mercaptotetrazole

(R)-methyl mandelate

Downstream raw materials:

(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

(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

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

Cefamandole nafate

Refernces

• 1、 Serra, Immacolata,Ceechini, Davide A.,UbiaIi, Daniela,Manazza, Elena M.,Albertini, Alessandra M.,Terreni, Marco. "Coupling of Site-Directed mutagenesis and immobilization for the rational design of more efficient biocatalysts: The case of immobilized 3G3K PGA from E. coli". . p. 1384 - 1389. Retrieved 2009.
• 2、 -. "PROCESS FOR THE PREPARATION OF CEFAMANDOLE NAFATE". Page/Page column 9. . Retrieved 2013/05/09.
• 3、 Terreni, Marco,Tchamkam, Joseph Gapesie,Sarnataro, Umberto,Rocchietti, Silvia,Fernandez-Lafuente, Roberto,Guisan, Jose M.. "Influence of substrate structure on PGA-catalyzed acylations. Evaluation of different approaches for the enzymatic synthesis of cefonicid". . p. 121 - 128. Retrieved 2007/10/03.