771456-08-7

Upstream product

• 67-56-1 methanol 
• 1186-90-9 L-threo-3-hydroxyaspartic acid 
• 1186-90-9 erythro-β-hydroxy-DL-aspartic acid 
• 7298-98-8 2-(S)-amino-3-(R)-hydroxysuccinic acid 

Relevant academic research and scientific papers

Structure and total synthesis of lysobactin (katanosin B)

(Chemical Equation Presented) Tackle-resistant bacteria: Determination of the 3D structure of the antibiotic lysobactin has led to its total synthesis and resulted in a high-yielding macrolactamization step. The minimal use of protecting groups allowed pr

An operationally simple and efficient synthesis of orthogonally protected L-threo-β-hydroxyasparagine

A synthesis of orthogonally protected L-threo-β-hydroxyasparagine from L-aspartic acid is reported. Iodocyclization of 3-benzoylaminoaspartic acid provided an intermediate oxazoline dicarboxylate that was efficiently hydrolyzed to L-threo-β-hydroxyasparti

MONOCYCLIC BETA-LACTAMS AND PROCESS FOR THE PREPARATION THEREOF

Monocyclic beta-lactam compounds represented by the formula STR1 wherein R 1 is H, NH 2, acylamino, C 1 -C 4 alkyl, etc.; R 2 is e.g. C 1 -C 4 alkyl, hydroxyalkyl, aminoalkyl, carboxy, esterified carboxy, esterified carboxyalkyl, or carboxyalkyl; and R 3 is hydrogen, benzyl, substituted benzyl, pivaloyl, --SO 3 M, or --P(C-O)(OM')2; are obtained by the cyclization of an O-substituted hydroxamate of a beta-substituted alkylcarboxylic acid. For example, alpha-ethylmalic acid monobenzyl ester is reacted with O-benzylhydroxylamine to form the O-benzylhydroxamate of the free carboxy group, and the hydroxamate is cyclized with diethyl diazodicarboxylate and triphenylphosphine to form the beta-lactam of the above formula wherein R 1 is ethyl, R 2 is benzyloxycarbonyl and R 3 is benzyl. The beta-lactam compounds are useful intermediates for preparing beta-lactamase inhibitors and monocyclic beta-lactam antibiotics and, when R 3 is --SO 3 M or -P(C-O)(OM')2 the compounds and salts thereof are antibacterial agents.