Generalized Anomeric Effect in gem-Diamines: Stereoselective Synthesis of α-N-Linked Disaccharide Mimics
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- 作者：Elena M. Snchez-Fernndez ; Roco Rsquez-Cuadro ; Matilde Aguilar-Moncayo ; M. Isabel Garca-Moreno ; Carmen Ortiz Mellet ; Jos M. Garca Fernndez
- 刊名：Organic Letters
- 出版年：2009
- 出版时间：August 6, 2009
- 年：2009
- 卷：11
- 期：15
- 页码：3306-3309
- 全文大小：192K
- 年卷期：v.11,no.15(August 6, 2009)
- ISSN：1523-7052
文摘
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 α-N-linked azadisaccharide heteroanalogues of the natural disaccharides maltose and isomaltose as aglycon-sensitive inhibitors of isomaltase.