62263-89-2Relevant academic research and scientific papers
Syntheses of (6S)-cephalosporins from 6-aminopenicillanic acid
Fekner, Tomasz,Baldwin, Jack E,Adlington, Robert M,Jones, Timothy W,Prout, C.Keith,Schofield, Christopher J
, p. 6053 - 6074 (2007/10/03)
Two practical routes to (6S,7S)-cephalosporins from 6-aminopenicillanic acid (6-APA) are described. In the first, 6-APA was converted to (2S,4S,5S,6S)-penicillin sulfoxide 49, which underwent Morin ring expansion to a protected (6S,7S)-cephem 50. In the s
EFFICIENT PREPARATION OF PENICILLANATE ESTER: A REDUCTIVE DEBROMINATION OF BROMOPENICILLANATE ESTER AND BROMOPENICILLANATE-S,S-DIOXIDE ESTER WITH TRI-N-BUTYLPHOSPHINE
Chern, Ji-Wang,Huang, Min,Tien, Jung-Hsiung,Pai, Shou-Hsiung
, p. 1349 - 1352 (2007/10/02)
Benzyl bromopenicillanate (5) and benzyl bromopenicillanate-S,S-dioxide (6) were subject to a reductive debromination in an effect of tri-n-butylphosphine furnishing benzyl penicillanate (7) and benzyl penicillanate-S,S-dioxide (8) in 50percent and 81percent yield respectively.
STEREOSELECTIVE PREPARATION OF 6β-SUBSTITUTED PENICILLANATES. TRI-ORGANOTIN HYDRIDE REDUCTION OF 6-ISOCYANO-, 6-PHENYLSELENENYL-, 6-HALO-, AND 6-ISOTHIOCYANATO-PENICILLANATES
John, D. Ivor,Tyrrell, Nicholas D.,Thomas, Eric J.
, p. 2477 - 2484 (2007/10/02)
6β-Benzyl-, 6β-(2-hydroxyprop-2-yl)-, 6β-methoxycarbonylmethyl-, 6β-methoxycarbonylethyl-, 6β-(t-butoxycarbonylmethyl)-, and 6β-methylthiopenicillanates 10-15 have been prepared stereoselectively by tri-n-butyltin hydride reduction of the corresponding 6β-isocyanopenicillanates 4-9.A minor side-product (15percent) isolated from the reduction of benzyl 6α-(2-hydroxyprop-2-yl)-6β-isocyanopenicillanate 5 was identified as (1R,5R)-6--1-(2-hydroxyprop-2-yl)-2,6-diaza-4-thiabicyclohept-2-en-7-one 18, and small quantities of analogous thiazolines 19 and 20 were detected in the crude mixtures from the reductions of the 6α-benzyl- and 6α-methoxycarbonylmethyl-6β-isocyanopenicillanates 4 and 6.Benzyl and methyl penicillanates 30 and 31 were obtained by tri-n-butyltin hydride reduction of the 6α-brompenicillanates 28 and 29, and reduction of benzyl 6,6-dibromopenicillanate 35 gave a mixture of products in wich the 6β-bromopenicillanate 37 predominated. 6β-Chloro-, 6β-phenylselenenyl-, and 6β-allylpenicillanates 48, 49 and 52 were obtained by tri-n-butyltin hydride reduction of the corresponding 6-phenyl- selenenylpenicillanates 43, 45, 50 and 51. In contrast, tri-organotin hydride reduction of methyl 6β-isothiocyanatopenicillanate 53 was accompanied by sulphur-C(2) bond cleavage to give rearranged thiazoline-azetidinones 54 and 55.
DERIVATIVES OF 6BETA-HYDROXYALKYLPENICILLANIC ACIDS AS BETA-LACTAMASE INHIBITORS
-
, (2008/06/13)
6beta-Hydroxyalkylpenicillanic acids and derivatives thereof as useful enhancers of the effectiveness of several beta-lactam antibiotics against many beta-lactamase producing bacteria, and 6beta-substituted penicillanic acid benzyl ester derivatives as useful intermediates leading to said agents which enhance the effectiveness of beta-lactam antibiotics
6-Substituted methyl penicillins, derivatives and analogues thereof
-
, (2008/06/13)
Disclosed are antibiotic 6-(substituted methyl) penicillins, derivatives and nuclear analogues thereof; wherein the methyl substituent is, inter alia, hydroxyl, ketonic oxygen, imino nitrogen, amino or thio. Also disclosed are processes for the preparatio
