NITROACETYL GROUP AS A PEPTIDE SYNTHON - SYNTHESIS OF DIPEPTIDES WITH AN ALPHA,ALPHA-BISALLYLGLYCINE RESIDUE AT THE N-TERMINUS

被引:15
作者
MANJUNATHA, SG [1 ]
CHITTARI, P [1 ]
RAJAPPA, S [1 ]
机构
[1] NATL CHEM LAB,DIV ORGAN CHEM SYNTH,POONA 411008,MAHARASHTRA,INDIA
关键词
D O I
10.1002/hlca.19910740516
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
N-Nitroacetyl derivatives of L-proline, L-valine, and L-phenylalanine esters were prepared in two steps under mild conditions (Scheme 2). Regiospecific mono- and bis-allylation of these nitroacetyl derivatives were accomplished in presence of a Pd(0) catalyst. The bis-allyl derivatives 7-9 were obtained in 40-75% yield. The tertiary NO2 group in these compounds could be transformed into an acetylamino group by Zn/AcOH/AC2O. The final products 11-13 are dipeptides in which the N-terminal glycine residue bears two alpha-allyl substituents.
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页码:1071 / 1080
页数:10
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