ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Preparation of Enantiomerically Pure Derivatives of 3-Amino- and 3-Mercaptobutanoic Acid by SN2 Ring Opening of the β-Lactone and a 1,3-Dioxanone Derived from 3-Hydroxybutanoic AcidFrom (S)-4-methyloxetan-2-one (1), the β-butyrolactone readily available from the biopolymer (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 N-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 SN2 ring opening with benzylamine to give the N-benzyl derivative (ent-5) of (S)-3-aminobutanoic acid in 30-40% yield.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19870700514
