24960-20-1Relevant articles and documents
Stereocontrolled synthesis of erythro N-protected α-amino epoxides and peptidyl epoxides
Albeck, Amnon,Persky, Rachel
, p. 6333 - 6346 (1994)
N-protected α-amino epoxides of erythro configuration, derived from α-amino acids, were synthesized in a stereoselective manner. The erythro (2S,3S), configuration was achieved by the synthetic sequence: amino acid -> haloketone -> halohydrin -> epoxide. A mechanistic explanation for the observed stereoselectivity is presented. This stereoselective synthetic approach was applied to the synthesis of a variety of short peptidyl epoxides, bearing a predefined absolute configuration of the chiral epoxide moiety.