Synthesis and reactions of fluorous carbobenzyloxy (FCbz) derivatives of alpha-amino acids.
Fluorous carbobenzyloxy ((F)Cbz) reagents RfCH(2)CH(2)C(6)H(4)CH(2)OC(O)OSu (where Su is succinimidoyl and Rf is C(6)F(13) and C(8)F(17)) have been used to make (F)Cbz derivatives of 18 of the 20 natural amino acids. The potential utility of this new family of reagents in both standard fluorous synthesis with spe separation and fluorous quasiracemic synthesis is illustrated with representative reactions of the (F)Cbz-Phe derivatives.
Curran
Dennis P
DP
Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA. curran@pitt.edu
Amatore
Muriel
M
Guthrie
David
D
Campbell
Matthew
M
Go
Eisan
E
Luo
Zhiyong
Z
D000596:Amino Acids / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D005459:Fluorides / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
D000596:Amino Acids; D001555:Benzene Derivatives; D007202:Indicators and Reagents; D005459:Fluorides