Title
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Isomerization of benzyl 6-phenoxyacetoxypenicillanates and their S-oxides
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Author
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Abstract
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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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Language
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English
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Source (journal)
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Journal of the Chemical Society : Perkin transactions I. - London, 1972 - 1999
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Publication
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London
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Chemical Society
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1976
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ISSN
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0300-922X
[print]
2050-8255
[online]
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DOI
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10.1039/P19760000704
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Volume/pages
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6
(1976)
, p. 704-710
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ISI
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A1976BM85400029
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Full text (Publisher's DOI)
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