Synthesis Using A-Alkoxycarbonylamino-Acid Fluorides

FIGURE 7.19 Reagents for preparing A-protected amino-acid fluorides,55-5661 Boc2-amino-acid fluorides (CyNF),58-59 and a nonbasic acid scavenger (BSA).62 CyNF = cyanuric fluoride DAST = diethylaminosulfur trifluoride TFFH = tetramethylfluoroformamidinium hexafluo-rophosphate BSA = b (trimethylsilyl)acetimide. 

LA Carpino, D Sadat-Aalaee, HG Chao, RH DeSelms. ((9-Fluorenylmethyl)oxy)car-bonyl (FMOC) amino acid fluorides. Convenient new peptide coupling reagents applicable to the FMOC/ferf-butyl strategy for solution and solid-phase syntheses. J Am Chem Soc 112, 9651, 1990. 

J-N Bertho, A Loffet, C Pinel, F Reuther, G Sennyey. Amino acid fluorides their preparation and use in peptide synthesis. Tetrahedron Lett 32, 1303, 1991. 

LA Carpino, EME Mansour, D Sadat-Aalaee. lerl-WutoxycarbonyI and benzyloxy-carbonyl amino acid fluorides. New, stable rapid-acting acylating agents for peptide synthesis. J Org Chem 56, 2611, 1991. 

J Savrda, M Wakselman. A-Alkoxycarbonylamino acid /V-carboxyanhydridcs and ALV-dialkoxycarbonyl amino acid fluorides from /V,/V-diprotcctcd amino acids. J Chem Soc Chem Commun 812, 1992. 

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