Generalized Anomeric Effect in gem-Diamines: Stereoselective Synthesis of α-N-Linked Disaccharide Mimics

被引:33
作者
Sanchez-Fernandez, Elena M. [2 ]
Risquez-Cuadro, Rocio [1 ]
Aguilar-Moncayo, Matilde [1 ]
Garcia-Moreno, M. Isabel [1 ]
Ortiz Mellet, Carmen [1 ]
Garcia Fernandez, Jose M. [2 ]
机构
[1] Univ Seville, Dept Quim Organ, Fac Quim, E-41071 Seville, Spain
[2] CSIC, Inst Invest Quim, E-41092 Seville, Spain
关键词
BIOLOGICAL EVALUATION; GLYCOSIDASE INHIBITORS; MALTASE-GLUCOAMYLASE; CRYSTAL-STRUCTURE; 1-N-IMINOSUGARS; GLUCOSIDASE; DERIVATIVES; GLYCOSYL; GLYCOMIMETICS; EFFICIENT;
D O I
10.1021/ol901125n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The orbital (negative hyperconjugation) contribution to the generalized anomeric effect is highly increased In bicyclic gem-diamines with a pseudoamide-type endocyclic nitrogen atom, which has been exploited for the stereoselective synthesis of configurationally stable alpha-N-linked azadisaccharide heteroanalogues of the natural disaccharides maltose and isomaltose as aglycon-sensitive inhibitors of isomaltase,
引用
收藏
页码:3306 / 3309
页数:4
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