63837-21-8Relevant articles and documents
Clavulanic Acid and its Derivatives. Structure Elucidation of Clavulanic Acid and the Preparation of Dihydroclavulanic Acid, Isoclavulanic acid, Esters and Related Oxidation Products
Brown, Allan G.,Corbett, David F.,Goodacre, Jennifer,Harbridge, John B.,Howarth, T. Trefor,et al.
, p. 635 - 650 (2007/10/02)
Clavulanic acid, a novel β-lactamase inhibitor from Streptomyces clavuligerus, has been shown to be Z-(2R,5R)-3-(β-hydroxyethylidene)-7-oxo-4-oxa-1-azabicycloheptane-2-carboxylic acid (1).The structure and absolute stereochemistry was confirmed by X-ray analysis of the p-nitrobenzyl and p-bromobenzyl esters, (14) and (15).The conversion of clavulanic acid into a variety of esters and acyl derivatives is described.An account of its isomerisation to the E isomer (30) and the formation of an oxetane (45) as a by-product of the photolysis of the phenacyl ester (18) is given.The reduction and oxidation of acid (1) under a variety of conditions has also been examined in detail.
Wittig Reactions with β-Lactam Carbonyls: A Convenient Means of Protection. X-Ray Crystal Structure of p-Nitrobenzyl-(2R,5R)-Z-7-Methoxycarbonylmethylene-Z-3-(β-phthalimidoethylidene)-4-oxa-1-azabicycloheptane-2-carboxylate
Gilpin, Martin L.,Harbridge, John B.,Howarth, T. Trefor,King, Trevor J.
, p. 929 - 930 (2007/10/02)
Clavulanic acid derivatives and penicillin V esters undergo Wittig reactions at the β-lactam carbonyl and the β-lactam can be regenerated by low-temperature ozonolysis; the crystal structure of one of the products is reported.