Herstellung enantiomerenreiner Derivate von 3-Amino- und 3-Mercaptobuttersaeure durch SN2-Ringoeffnung des β-Lactons und eines 1,3-Dioxanons aus der 3-Hydroxybuttersaeure

Article abstract of DOI:10.1002/hlca.19870700514

From (S)-4-methyloxetan-2-one (1), the β-butyrolactone readily available from the biopolyner (R)-polyhydroxybutyrate (PHB) and various C,N,O and S nucleophiles, the following compounds are prepared: (S)-2-hydroxy-4-octanone (3), (R)-3-aminobutanoic acid (7) and its benzyl derivative 5, (R)-3-azidobutanoic acid (6), (R)-3-mercaptobutanoic acid (10), (R)-3-(phenylthio)butanoic acid (8) and its sulfoxide 9.The (6R)-2,6-dimethyl-2-ethoxy-1,3-dioxan-4-one (4) from (R)-3-hydroxybutanoic acid undergoes S_N2 ring opening with benzylamine to give the N-benzyl derivative (ent-5) of (S)-3-aminobutanoic acid in 30-40percent yield.