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Synthesis of Multibranched Australine Derivatives from Reducing Castanospermine Analogues through the Amadori Rearrangement of gem-Diamine Intermediates: Selective Inhibitors of β-Glucosidase.
- Source :
-
Journal of Organic Chemistry . 12/5/2014, Vol. 79 Issue 23, p11722-11728. 7p. - Publication Year :
- 2014
-
Abstract
- A practical one-pot synthesis of bi- and triantennated australine analogues from a pivotal sp²-iminosugar-type reducing castanospermine precursor is reported. The transformation involves a gem-diamine intermediate that undergoes the indolizidine → pyrrolizidine Amadori-type rearrangement and proceeds under strict control of the generalized anomeric effect to afford a single diastereomer. The final compounds behave as selective competitive inhibitors of β-glucosidase and are promising candidates as pharmacological chaperones for Gaucher disease. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 79
- Issue :
- 23
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 100052808
- Full Text :
- https://doi.org/10.1021/jo5025283