616215-36-2Relevant academic research and scientific papers
Total synthesis of (+)-valienamine and (-)-1-epi-valienamine via a highly diastereoselective allylic amination of cyclic polybenzyl ether using chlorosulfonyl isocyanate
Li, Qing Ri,Kim, Seung In,Park, Sook Jin,Yang, Hye Ran,Baek, A Reum,Kim, In Su,Jung, Young Hoon
, p. 10384 - 10390 (2013/11/19)
The total synthesis of (+)-valienamine and (-)-1-epi-valienamine was concisely accomplished from readily available d-glucose via a highly diastereoselective amination of chiral benzylic ether using chlorosulfonyl isocyanate, intramolecular olefin metathesis, and diastereoselective reduction of cyclic enone using l-Selectride as the key steps.
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.
Iminosugar analogues of phosphatidyl inositol as potential inhibitors of protein kinase B (Akt)
Orsato, Alexandre,Barbagallo, Emanuela,Costa, Barbara,Olivieri, Sandro,De Gioia, Luca,Nicotra, Francesco,La Ferla, Barbara
, p. 5012 - 5019 (2011/11/14)
A small virtual library of iminosugar derivatives was evaluated by docking experiments carried out by sampling a protein region corresponding to the phosphoinositide binding site of the PH domain of Akt. Four compounds were selected and efficiently synthesised from a common precursor. All compounds were subjected to preliminary biological evaluation on purified enzyme, and - among them - compound 9 exhibited the best inhibitory activity. A small virtual library of iminosugar-based Akt inhibitors have been designed and evaluated by using docking calculations. Selected compounds have been conveniently synthesised, and preliminary biological evaluation identified compound 9 as a possible lead compound for further development of iminosugar-based Akt inhibitors. Copyright
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
