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Synthesis of Glycomimetics by Diastereoselective Passerini Reaction

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

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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
Uncontrolled Keywords: multicomponent reactions; Passerini reaction; D-fructose; glycomimetics
Subjects: NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
NMR Center
Project titleProject leaderProject codeProject type
Višekomponentne reakcije u sintezi peptidnih mimetika-MIMICRyIVANKA JERIĆIP-2014-09-3102HRZZ
Depositing User: Ivanka Jerić
Date Deposited: 19 Nov 2019 12:53
DOI: 10.1021/acs.joc.8b01874

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