Monatshefte für Chemie / Chemical Monthly

, Volume 122, Issue 5, pp 389–398 | Cite as

Markierte Vertreter eines möglichen Zwischenprodukts der Biosynthese von Fosfomycin inStreptomyces fradiae: Darstellung von (R,S)-(2-Hydroxypropyl)-, (R,S)-, (R)-, (S)-(2-Hydroxy-[1,1-2H2]propyl)-und (R,S)-(2-[18O]Hydroxypropyl)phosphonsäure

  • Friedrich Hammerschmidt
Organische Chemie Und Biochemie
Received:
Accepted:

Labelled representatives of a possible intermediate of fosfomycin biosynthesis inStreptomyces fradiae: Preparation of (R,S)-(2-hydroxypropyl)-, (R,S)-, (R)- and (S)-(2-hydroxy-[1,1-2H2]propyl)- and (R,S)-(2-[18O]hydroxypropyl)phosphonic acid

Summary

Racemic methyl O-benzyllactate was reduced to the alcohol, transformed into the bromide and reacted with triethylphosphite to give the diethylphosphonate. Removal of protecting groups afforded a phosphonic acid which was purified as its cyclohexylammonium salt. (S)-Ethyl and (R)-isobutyl O-benzyllactate were reduced with LiAlD4 to the corresponding dideuteriated alcohols, which were transformed in the same way as the racemic compound into the chiral (2-hydroxy-[1,1-2H2]propyl)phosphonic acids. The optical purity of alcohols (S)- and (R)-6 b was determined by derivatisation with (+)-MTPA-Cl and1H-NMR-spectroscopy to be 98%. Exchange of the carbonyl-16-oxygen atom of 2-oxopropylphosphonate for oxygen-18 from H218O, reduction with NaBH4, deprotection and addition of cyclohexylamine yielded the salt (±)-18 of (2-[18O]hydroxypropyl)phosphonic acid.

Keywords

(2-Hydroxypropyl)phosphonic acids Deuterium-labelling of 18O-labelling of Chiral lactates 
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Copyright information

© Springer-Verlag 1991

Authors and Affiliations

  • Friedrich Hammerschmidt
    • 1
  1. 1.Institut für Organische ChemieUniversität WienWienÖsterreich

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