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Acyloxymethyl as a drug protecting group. Kinetics and mechanism of the hydrolysis of N-acyloxymethylbenzamides

โœ Scribed by Iley, Jim; Moreira, Rui; Rosa, Eduarda


Book ID
121254162
Publisher
Royal Society of Chemistry
Year
1991
Tongue
English
Weight
865 KB
Volume
5
Category
Article
ISSN
1472-779X

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Acyloxymethyl as a drug protecting group
โœ Teresa Calheiros; Jim Iley; Francisca Lopes; Rui Moreira ๐Ÿ“‚ Article ๐Ÿ“… 1995 ๐Ÿ› Elsevier Science ๐ŸŒ English โš– 213 KB

Tertiary N-acyloxymethylsulfonamide prodrugs 3, encompassing penicillin and sulfonamide antibiotics, have been synthesised. The pH-independent hydrolysis of these compounds ocurrs via the rate-determining formation of an N-sulfonyl iminium ion. SCF-MO calculations using the PM3 method indicate that