m-Chloroperbenzoic acid → Phe-Pro

Participants

Reaction Steps

Eventually, using the benzyl 3-((2S,3S)-3-{[(1S,2S)-1-hydroxy-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}oxiran-2-yl)propylcarbamate, recoverable as a by-product from the epoxidation with m-chloroperbenzoic acid of the allylic alcohol (4E,6R,7S)-7-[(tert-butoxycarbonyl)amino]-6-hydroxy-8-phenyl-oct-4-enylcarbamate (8), and following an approach similar to the one already described for the synthesis of tert-butyl (1S,2S,3S)-1-benzyl-2,3-dihydroxy-3-[(2S)-pyrrolidin-2-yl]propylcarbamate (10), tert-butyl (1S,2S,3R)-1-benzyl-2,3-dihydroxy-3-[(2R)-pyrrolidin-2-yl]propylcarbamate can be obtained as a possible fourth diaminodiol (S,S,R,R) Phe-Pro isostere.

Provenance & Evidence