Title
Isomerization of benzyl 6-phenoxyacetoxypenicillanates and their S-oxides
Author
Faculty/Department
Faculty of Pharmaceutical, Biomedical and Veterinary Sciences. Pharmacy
Publication type
article
Publication
London ,
Subject
Chemistry
Source (journal)
Journal of the Chemical Society: Perkin transactions 1: organic and bio-organic chemistry. - London, 1972 - 1999
Volume/pages
(1976) :6 , p. 704-710
ISSN
0300-922X
ISI
A1976BM85400029
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
The preparation of benzyl 6α- and 6β-phenoxyacetoxypenicillanate and their (S)- and (R)-S-oxides is described. No epimerisation was observed when benzyl 6α- or 6β-phenoxyacetoxypenicillanate or benzyl 6α- or 6β-trimethylsiloxypenicillanate was treated with 1,5-diazabicyclo[4.3.0]non-5-ene (DBN). Benzyl 6β-phenoxyacetoxypenicillanate (S)-S-oxide was transformed into the 6α-isomer with DBN as catalyst; the converse reaction was not observed. With both isomers in these experiments, the phenoxyacetoxy side chain was hydrolysed to a large extent.
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