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The Staudinger/aza-Wittig/Grignard reaction as key step for the concise synthesis of 1-C-Alkyl-iminoalditol glycomimetics.
- Source :
-
Carbohydrate Research . Jun2016, Vol. 429, p62-70. 9p. - Publication Year :
- 2016
-
Abstract
- The scope of a one-pot tandem approach for the synthesis of C-1 alkyl iminoalditol derivatives with a Staudinger/aza-Wittig/Grignard cascade has been evaluated. The reaction conditions have been optimized for two azidodeoxy aldose substrates and a range of Grignard reagents. The nature of both, substrate as well as nucleophile, was found to control the stereoselectivity of the alkyl addition to the cyclic iminium intermediate at position C-1. This approach enabled the synthesis of a collection of C -alkyl iminoalditols, which were biologically evaluated as inhibitors against a set of standard glycoside hydrolases. All compounds were found to exhibit highly selective inhibition of β-glucosidase activity. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00086215
- Volume :
- 429
- Database :
- Academic Search Index
- Journal :
- Carbohydrate Research
- Publication Type :
- Academic Journal
- Accession number :
- 115824339
- Full Text :
- https://doi.org/10.1016/j.carres.2016.04.006