76517-36-7

Upstream product

• 75722-77-9 6-alpha-trifluoromethylsulfonyloxypenicillanic acid benzhydryl ester 
• 76517-35-6 6,6-diiodopenicillanic acid benzhydryl ester 

Downstream Products

• 74772-32-0 6β-iodopenicillanic acid 

Relevant academic research and scientific papers

6-β-substituted penicillanic acid compound free of the 6-α-epimer

6-β-Substituted penicillanic acids and derivatives thereof as useful enhancers of the effectiveness of several β-lactam antibiotics against many β-lactamase producing bacteria, and 6-β-substituted penicillanic acid derivatives wherein the carboxy group is protected by a conventional penicillin carboxy protecting group as useful intermediates leading to said synergistic agents. A process for converting 6,6-disubstituted penicillanic acid derivatives to the corresponding 6-β-substituted penicillanic acid congeners.

6-beta-Halopenicillanic acid 1,1-dioxides as beta-lactamase inhibitors

6-beta-Halopenicillanic acid 1,1-dioxides, physiologically acceptable salts thereof and esters thereof readily hydrolyzable; pharmaceutical compositions containing a 6-beta-halopenicillanic acid 1,1-dioxide, a physiologically acceptable salt thereof or an ester thereof readily hydrolyzable; and a method for enhancing the effectiveness of a beta-lactam antibiotic, using a 6-beta-halopenicillanic acid 1,1-dioxide, a physiologically acceptable salt thereof or an ester thereof readily hydrolyzable.

6-Alpha-halopenicillanic acid 1,1-dioxides

A process for the preparation of penicillanic acid 1,1-dioxide and esters thereof readily hydrolyzable in vivo, which comprises oxidation of a 6-halopenicillanic acid, or an ester thereof readily hydrolyzable in vivo, to the corresponding 6-halopenicillanic acid 1,1-dioxide or ester thereof, followed by dehalogenation (e.g. by hydrogenolysis). Certain of the 6-halopenicillanic acid 1,1-dioxides and esters thereof readily hydrolyzable in vivo are novel intermediates. Penicillanic acid 1,1-dioxide, and esters thereof readily hydrolyzable in vivo are known compounds which are beta-lactamase inhibitors and which enhance the effectiveness of certain beta-lactam antibiotics (e.g. the penicillins) in the treatment of bacterial infections in mammals, particularly humans.

Process for converting 6,6-disubstituted penicillanic acid derivatives to the 6-β-congeners

6-β-Substituted penicillanic acids and derivatives thereof as useful enhancers of the effectiveness of several β-lactam antibiotics against many β-lactamase producing bacteria, and 6-β-substituted penicillanic acid derivatives wherein the carboxy group is protected by a conventional penicillin carboxy protecting group as useful intermediates leading to said synergistic agents. A process for converting 6,6-disubstituted penicillanic acid derivatives to the corresponding 6-β-substituted penicillanic acid congeners.

6-Perhaloalkylsulfonyloxy-penicillanic acids and derivatives thereof

6-Alpha and 6-beta-substituted penicillanic acid derivatives of the formula: STR1 wherein R is H or a conventional penicillin carboxy protecting group or an ester forming residue readily hydrolyzable in vivo and R1 is a perhaloalkyl group of from 1 to 4 carbon atoms wherein the halogen atoms are fluoro or chloro, undergo SN2 nucleophilic displacement with halide or azide ions with inversion of configuration at C-6 to yield the corresponding 6-beta or 6-alpha-halo- or azido-substituted product.