Synthesis of aza-C-disaccharides using cycloaddition reactions of a functionalized cyclic nitrone

被引:40
作者
Duff, FJ [1 ]
Vivien, V [1 ]
Wightman, RH [1 ]
机构
[1] Heriot Watt Univ, Dept Chem, Edinburgh EH14 4AS, Midlothian, Scotland
关键词
D O I
10.1039/b005984f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cycloaddition reactions of a functionalized nitrone with sugar alkenes gives stereoselective access to aza-C-disaccharide analogues of alpha -d-Lyx(1 -->6)-alpha -d-Man and alpha -d-Lyx(1 -->6)-d-Gal.
引用
收藏
页码:2127 / 2128
页数:2
相关论文
共 26 条
[1]   A FACILE, PRACTICAL SYNTHESIS OF 2,6-DIDEOXY-2,6-IMINO-7-O-BETA-D-GLUCOPYRANOSYL-D-GLYCERO-L-GULO-HEPTITOL (MDL 25,637) [J].
ANZEVENO, PB ;
CREEMER, LJ ;
DANIEL, JK ;
KING, CHR ;
LIU, PS .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) :2539-2542
[2]   Conformational behavior of aza-C-glycosides:: Experimental demonstration of the relative role of the exo-anomeric effect and 1,3-type interactions in controlling the conformation of regular glycosides [J].
Asensio, JL ;
Cañada, FJ ;
García-Herrero, A ;
Murillo, MT ;
Fernández-Mayoralas, A ;
Johns, BA ;
Kozak, J ;
Zhu, ZZ ;
Johnson, CR ;
Jiménez-Barbero, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) :11318-11329
[3]  
BLAKE AJ, 1993, J CHEM RES-S, P482
[4]  
BLAKE AJ, 1993, J CHEM RES M, P3173
[5]   1,3-AMINOALCOHOLS BY REDUCTIVE CLEAVAGE OF ISOXAZOLIDINES WITH MOLYBDENUM HEXACARBONYL [J].
CICCHI, S ;
GOTI, A ;
BRANDI, A ;
GUARNA, A ;
DESARLO, F .
TETRAHEDRON LETTERS, 1990, 31 (23) :3351-3354
[6]   ALPHA-GLUCOSIDASE INHIBITION IMPROVES POSTPRANDIAL HYPERGLYCEMIA AND DECREASES INSULIN REQUIREMENTS IN INSULIN-DEPENDENT DIABETES-MELLITUS [J].
DIMITRIADIS, GD ;
TESSARI, P ;
GO, VLW ;
GERICH, JE .
METABOLISM-CLINICAL AND EXPERIMENTAL, 1985, 34 (03) :261-265
[7]   Evaluation of isofagomine and its derivatives as potent glycosidase inhibitors [J].
Dong, WL ;
Jespersen, T ;
Bols, M ;
Skrydstrup, T ;
Sierks, MR .
BIOCHEMISTRY, 1996, 35 (08) :2788-2795
[8]  
Goss PE, 1995, CLIN CANCER RES, V1, P935
[9]   N-ACETYLGLUCOSAMINONO-1,5-LACTONE OXIME AND THE CORRESPONDING (PHENYLCARBAMOYL)OXIME - NOVEL AND POTENT INHIBITORS OF BETA-N-ACETYLGLUCOSAMINIDASE [J].
HORSCH, M ;
HOESCH, L ;
VASELLA, A ;
RAST, DM .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1991, 197 (03) :815-818
[10]  
HUMPHRIES MJ, 1986, CANCER RES, V46, P5215