First synthesis of totally orthogonal protected alpha-(trifluoromethyl)- and alpha-(difluoromethyl)arginines.
The first synthesis of a series of totally orthogonal protected racemic alpha-(trifluoromethyl)- and alpha-(difluoromethyl)arginines is described. The key steps of the synthesis are the mild guanidinylation procedure and the selective hydrogenation of a CC triple bond in the presence of a Cbz-group.
Moroni
M
M
Institute of Organic Chemistry, University of Leipzig, Johannisallee 29, D-04103 Leipzig, Germany. moroni@organik.chemie.uni-leipzig.de
Koksch
B
B
Osipov
S N
SN
Crucianelli
M
M
Frigerio
M
M
Bravo
P
P
Burger
K
K
D001120:Arginine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D002855:Chromatography, Thin Layer; D006146:Guanidines / Q000737:chemistry; D006865:Hydrogenation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy
C431668:(trifluoromethyl)arginine; D006146:Guanidines; D007202:Indicators and Reagents; C030965:alpha-(difluoromethyl)arginine; D001120:Arginine