On the stereochemical purity of (+)-7-aminocephalosporanic acid

✍ Scribed by Thomas Oberhauser; Vladimir Meduna

• Book ID: 104207343
• Publisher: Elsevier Science
• Year: 1996
• Tongue: French
• Weight: 740 KB
• Volume: 52
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(96)00353-5

✦ Synopsis

+)-7-Aminocephalosporanic acid (18a) and (+)-7-epi-aminocephalosporanic acid (4a) have been synthesized. A chiral HPLC method has been developed for the separation of the four stereoisomers. Natural (+)-7-aminocephalosporanic acid (1) was demonstrated to be enantiomerically (ee >> 99.95%) and diastereomerically (de >>99.95%) pure. Copyright © 1996 Elsevier Science Ltd (+)-7-Aminocephalosporanic acid (7-ACA) (1) is the starting material for many semlsynthetic cephalosporins. Most of the estimated 1500 tons/year are produced from cephalosporin C (2) by chemical cleavage of the D-2-aminoadipic acid side chain) S.