Synthesis of orthogonally protected (3R, 4S)- and (3S, 4S)-4,5-diamino-3-hydroxypentanoic acids.
The paper describes two methods of the synthesis of ethyl (3R, 4S)- and (3S, 4S)-4-[(benzyloxycarbonyl)amino]-5-[( tert-butyloxycarbonyl)amino]-3-hydroxypentanoates, useful for the syntheses of edeine analogs. Differently N-protected (S)-2,3-diaminopropanoic acid was used as a substrate in both procedures. The absolute configuration of newly generated asymmetric carbon atoms C-3 in beta-hydroxy-gamma, delta-diamino products was assigned by means of (1)H NMR spectroscopy after their transformation into corresponding piperidin-2-ones.
Czajgucki
Z
Z
Department of Pharmaceutical Technology and Biochemistry, Technical University of Gdańsk, 11/12 Narutowicza Street, 80-952 Gdańsk, Poland. zmczaj@wp.pl
Sowiński
P
P
Andruszkiewicz
R
R
D000599:Amino Acids, Diamino / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010421:Pentanoic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C482319:4,5-diamino-3-hydroxypentanoic acid; D000599:Amino Acids, Diamino; D010421:Pentanoic Acids