Stereoselective syntheses of 4-amino-aldoses, and chiral pyrrolidine derivatives from glycosylenamines

被引:11
作者
Fuentes, J
Olano, D
Pradera, MA
机构
[1] Dpto. de Quim. Orgánica, Facultad de Química, Universidad de Sevilla, E-41071 Sevilla
关键词
D O I
10.1016/S0957-4166(97)00404-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The stereocontrolled synthesis of N-protected 4-amino-4-deoxy-D-galacto- and -L-arabino-pyranoses starting from glycosylenamines via aza-anhydropyranoses is described. The steroselective transformation of the intermediate aza-anhydropyranoses into chiral pyrrolidines is also reported. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:3443 / 3456
页数:14
相关论文
共 41 条
[1]   OXIDATION OF ENAMINES DERIVED FROM SUGARS [J].
BABIANO, R ;
DURAN, C ;
PLUMET, J ;
ROMAN, E ;
SANCHEZ, E ;
SERRANO, JA ;
FUENTES, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (11) :1923-1926
[2]   A NEW ROUTE TO CHIRAL HYDROXYPYRROLIDINES FROM D-ERYTHROSE VIA INTRAMOLECULAR 1,3-CYCLOADDITION [J].
BUCHANAN, JG ;
EDGAR, AR ;
HEWITT, BD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (11) :2371-2376
[3]   ENATIOSPECIFIC SYNTHESIS OF (+)-RETRONECINE, (+)-CROTONECINE, AND RELATED ALKALOIDS [J].
BUCHANAN, JG ;
JIGAJINNI, VB ;
SINGH, G ;
WIGHTMAN, RH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (11) :2377-2384
[4]  
Bundle DR., 1976, METHODS CARBOHYDRATE, V7, P79
[5]   THE UTILITY OF 2,5-DIDEOXY-2,5-IMINO-D-MANNITOL AS A PFP ENZYME-INHIBITOR [J].
CHORGHADE, MS ;
CSEKE, CT ;
LIU, PS .
TETRAHEDRON-ASYMMETRY, 1994, 5 (11) :2251-2254
[6]   SYNTHESIS OF AZASUGARS BY GRIGNARD REACTION ON GLYCOSYLAMINES [J].
CIPOLLA, L ;
LAY, L ;
NICOTRA, F ;
PANGRAZIO, C ;
PANZA, L .
TETRAHEDRON, 1995, 51 (16) :4679-4690
[7]  
DOBOSHI K, 1985, J ANTIBIOT, V38, P1166
[8]  
FERNANDEZ G, 1996, SULFUR REP, V19, P61
[9]   REGIOSELECTIVE GLYCOSYLATION OF N-PROTECTED L-RHAMNO(FUCO) PYRANOSYLAMINES - PREPARATION AND SPECTROSCOPIC CHARACTERIZATION OF BUILDING-BLOCKS FOR NEOGLYCOCONJUGATE SYNTHESES [J].
FUENTES, J ;
GONZALEZEULATE, E ;
LOPEZBARBA, E ;
ROBINA, I .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1995, 14 (01) :79-93
[10]   SYNTHESES OF O-PROTECTED 2-AMINO-2-DEOXY-GENTIOBIOSIDE HYDROHALIDES [J].
FUENTES, J ;
CUEVAS, T ;
PRADERA, MA .
TETRAHEDRON, 1993, 49 (28) :6235-6250