Publication
Title
Isomerization of benzyl 6-phenoxyacetoxypenicillanates and their S-oxides
Author
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.
Language
English
Source (journal)
Journal of the Chemical Society: Perkin transactions 1: organic and bio-organic chemistry. - London, 1972 - 1999
Publication
London : 1976
ISSN
0300-922X
Volume/pages
6(1976), p. 704-710
ISI
A1976BM85400029
Full text (Publisher's DOI)
UAntwerpen
Faculty/Department
Research group
Publication type
Subject
Affiliation
Publications with a UAntwerp address
External links
Web of Science
Record
Identification
Creation 18.11.2014
Last edited 12.06.2017
To cite this reference