Diastereoselective Synthesis of C-Glycosylated Amino Acids with Lactams as Peptide Building Blocks.
Readily available by lipase-catalyzed kinetic resolution or from a chiral pool, beta-, gamma-, and delta-lactams can be used as peptide building blocks for the synthesis of C-glycosylated amino acids 1. By reaction with glycosyl dianions, metabolic stable glycosylated amino acids can be prepared diastereoselectively. Ac=acetyl; Bn=benzyl; Boc=tert-butoxycarbonyl; R=Et, Bn; R'=H, alkyl; n=1-3.
Westermann
B
Fachbereich für Chemie und Chemietechnik der Universität-Gesamthochschule, Warburgerstrasse 100, D-33098 Paderborn (Germany).
Walter
A
Diedrichs
N