Vlahoviček-Kahlina, Kristina; Vazdar, Mario; Jakas, Andreja; Smrečki, Vilko; Jerić, Ivanka (2018) Synthesis of Glycomimetics by Diastereoselective Passerini Reaction. Journal of Organic Chemistry, 83 (21). pp. 13146-13156. ISSN 0022-3263
Official URL: https://pubs.acs.org/journal/joceah
Abstract
We describe the utilization of bis-isopropylidene-protected d-fructose-derived aldehyde in the Passerini reaction with various acids and isocyanides. A library of densely functionalized glycomimetics bearing up to 3 carbohydrate units was obtained in high yields and diastereoselectivities. The configuration of the newly formed stereocenter was determined and the diastereoselectivity was rationalized by DFT calculations.
| Item Type: | Article | ||||||||
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| Uncontrolled Keywords: | multicomponent reactions; Passerini reaction; D-fructose; glycomimetics | ||||||||
| Subjects: | NATURAL SCIENCES > Chemistry > Organic Chemistry | ||||||||
| Divisions: | Division of Organic Chemistry and Biochemistry NMR Center |
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| Depositing User: | Ivanka Jerić | ||||||||
| Date Deposited: | 19 Nov 2019 12:53 | ||||||||
| URI: | http://fulir.irb.hr/id/eprint/5070 | ||||||||
| DOI: | 10.1021/acs.joc.8b01874 |
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