Carboxylic Acid Analogues of Fosmidomycin

Carboxylic Acid Analogues of Fosmidomycin

N-Alkylation of N-Boc-O-benzylhydroxylamine (1) with benzyl 4-bromobutyrate (2) in DMF gave N,O-bisprotected benzyl 4-hydroxyamino-butyrate (3), which was converted into 4-benzyloxyamino-butyric acid benzyl ester (4) with TFA in methylene chloride. Treatment of 4 with formic acid/acetic anhydride or...

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Veröffentlicht in:Zeitschrift für Naturforschung. B, A journal of chemical sciences A journal of chemical sciences, 2003-05, Vol.58 (5), p.457-461
Hauptverfasser: Kurz, Thomas, Geffken, Detlef, Wackendorff, Claudia
Format: Artikel
Sprache:eng
Schlagworte:
4-(N-Acyl-N-hydroxyamino)- butyric Acids
Fosmidomycin
Non-mevalonate Isoprenoid Biosynthesis
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Zusammenfassung:N-Alkylation of N-Boc-O-benzylhydroxylamine (1) with benzyl 4-bromobutyrate (2) in DMF gave N,O-bisprotected benzyl 4-hydroxyamino-butyrate (3), which was converted into 4-benzyloxyamino-butyric acid benzyl ester (4) with TFA in methylene chloride. Treatment of 4 with formic acid/acetic anhydride or various acid chlorides followed by catalytic hydrogenation led to 4-(N-acyl-N-hydroxyamino)-butyric acids 6.
ISSN:0932-0776
1865-7117
DOI:10.1515/znb-2003-0517