Protection of hydroxyl in the synthesis of semisynthetic beta-lactam antibiotics. 1981

P W Woo

The 2-methoxypropan-2-yl group fulfills the need of a hydroxyl protecting group generally suitable for the synthesis of beta-lactam antibiotics, satisfying the criteria of low-cost, convenience and selectivity in formation, and, above all, ease of deprotection under conditions compatible to the highly sensitive beta-lactam function and without contamination of the final products. The use of this protecting group has enabled the successful attachment of 6-[4-(N-acetyl-4-hydroxyl-L-prolylamino)phenyl]-1,2-dihydro - 2 - oxo - 3 - pyridinecarboxyl group, through an amide linkage, to amoxicillin, cephaloglycin, and the 3[[(1-carboxymethyl)-1-H-tetrazol-5-yl]thio]methyl analogue of the latter, yielding broad-spectrum antibiotics with notably good activities against strains of Pseudomonas aeruginosa.

UI MeSH Term Description Entries
D011550 Pseudomonas aeruginosa A species of gram-negative, aerobic, rod-shaped bacteria commonly isolated from clinical specimens (wound, burn, and urinary tract infections). It is also found widely distributed in soil and water. P. aeruginosa is a major agent of nosocomial infection. Bacillus aeruginosus,Bacillus pyocyaneus,Bacterium aeruginosum,Bacterium pyocyaneum,Micrococcus pyocyaneus,Pseudomonas polycolor,Pseudomonas pyocyanea
D000900 Anti-Bacterial Agents Substances that inhibit the growth or reproduction of BACTERIA. Anti-Bacterial Agent,Anti-Bacterial Compound,Anti-Mycobacterial Agent,Antibacterial Agent,Antibiotics,Antimycobacterial Agent,Bacteriocidal Agent,Bacteriocide,Anti-Bacterial Compounds,Anti-Mycobacterial Agents,Antibacterial Agents,Antibiotic,Antimycobacterial Agents,Bacteriocidal Agents,Bacteriocides,Agent, Anti-Bacterial,Agent, Anti-Mycobacterial,Agent, Antibacterial,Agent, Antimycobacterial,Agent, Bacteriocidal,Agents, Anti-Bacterial,Agents, Anti-Mycobacterial,Agents, Antibacterial,Agents, Antimycobacterial,Agents, Bacteriocidal,Anti Bacterial Agent,Anti Bacterial Agents,Anti Bacterial Compound,Anti Bacterial Compounds,Anti Mycobacterial Agent,Anti Mycobacterial Agents,Compound, Anti-Bacterial,Compounds, Anti-Bacterial

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