127656-45-5Relevant academic research and scientific papers
The development of an aza-C-glycoside library based on a tandem staudinger/aza-wittig/ugi three-component reaction
Wennekes, Tom,Bonger, Kimberly M.,Vogel, Katrin,Van Den Berg, Richard J. B. H. N.,Van Der Marel, Gijsbert A.,Overkleeft, Herman S.,Strijland, Anneke,Donker-Koopman, Wilma E.,Aerts, Johannes M. F. G.
, p. 6420 - 6454,35 (2020/09/16)
We report the tandem Staudinger/aza-Wittig/Ugi three-component reaction mediated synthesis of a 64-member compound library of aza-C-glycosides. The library is composed of four pyrrolidine and three piperidine scaffolds, onto which a number of functional groups is grafted to form seven sublibraries. Variation in the library is achieved by transformation of two pentoses and a hexose into the corresponding 4-azidopentanal and 5-azidohexanal derivatives as precursors for the Staudinger/aza-Wittig process. Further variation is achieved by using different isocyanides as well as protective- and functional-group manipulations on the fully protected Ugi-3CR intermediates. Preliminary biological evaluation of the compound library revealed several low micromolar inhibitors of human acid glucosylceramidase.
Nitrogen inversion as a diastereomeric relay in azasugar synthesis: The first synthesis of adenophorine
Maughan, Michael A. T.,Davies, Ieuan G.,Claridge, Timothy D. W.,Courtney, Steve,Hay, Phil,Davis, Benjamin G.
, p. 3788 - 3792 (2007/10/03)
A temperature-dependent relay of chirality is based on the inversion of the nitrogen lone pair in cyclic azasugars. Elimination from the conformation preferred at a given temperature leads to a cyclic imine, and in a subsequent nucleophilic attack the ste
The synthesis of protected 5-azido-5-deoxy-D-glucononitriles as precursors of glycosidase inhibitors
Bird, P.,Dolphin, D. H.,Withers, S. G.
, p. 317 - 322 (2007/10/02)
The successful syntheses of 5-azido-2,3,4,6-tetra-O-benzyl-5-deoxy-D-glucononitrile and 2,3,4,6-tetra-O-benzyl-5-deoxy-5-trifluoroacetamido-D-glucononitrile starting from D-glucose are described.Unsuccessful attempts were made to convert these two compoun
