ETHYL TRIFLUOROACETATE - A POWERFUL REAGENT FOR DIFFERENTIATING AMINO-GROUPS

被引:75
作者
XU, DQ [1 ]
PRASAD, K [1 ]
REPIC, O [1 ]
BLACKLOCK, TJ [1 ]
机构
[1] SANTEN PHARMACEUT CO LTD,SANDOZ RES INST,CHEM RES & DEV TECH R&D,E HANOVER,NJ 07936
关键词
D O I
10.1016/0040-4039(95)01655-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Selective protection of primary amines in the presence of secondary amines and monofunctionalization of symmetric primary and secondary diamines using ethyl trifluoroacetate is described. Effective differentiation of primary, secondary and tertiary alkyl-substituted primary amines from one another by ethyl trifluoroacetate acylation is also demonstrated. These results are explained on the basis of steric and electronic effects of the substrate amines.
引用
收藏
页码:7357 / 7360
页数:4
相关论文
共 8 条
[1]  
AVIRONVIOLET P, 1990, Patent No. 4943679
[2]  
GREEN TW, 1991, PROTECTIVE GROUPS OR
[3]  
Mc Arnett E., 1950, J AM CHEM SOC, V72, P5635
[4]  
Mc Arnett E., 1951, J AM CHEM SOC, V73, P5393
[5]   DISCRIMINATION OF SPERMIDINE AMINO FUNCTIONS BY A NEW PROTECTING GROUP STRATEGY APPLICATION TO THE SYNTHESIS OF GUANIDINYLATED POLYAMINES, INCLUDING HIRUDONINE [J].
MITCHINSON, A ;
GOLDING, BT ;
GRIFFIN, RJ ;
OSULLIVAN, MC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (22) :2613-2614
[6]  
OSULLIVAN, 1995, TETRAHEDRON LETT, V36, P3451
[7]   REVERSIBLE PROTECTION OF LYSINE TO FACILITATE THE PURIFICATION OF PROTECTED PEPTIDE SEGMENTS [J].
RIZO, J ;
ALBERICIO, F ;
GIRALT, E ;
PEDROSO, E .
TETRAHEDRON LETTERS, 1992, 33 (03) :397-400
[8]  
WERNER BHH, 1968, ANGEW CHEM INT EDIT, V7, P817