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Multicomponent approach to homo- and hetero-multivalent glycomimetics bearing rare monosaccharides

Jakas, Andreja; Višnjevac, Aleksandar; Jerić, Ivanka (2020) Multicomponent approach to homo- and hetero-multivalent glycomimetics bearing rare monosaccharides. Journal of Organic Chemistry, 85 (5). pp. 3766-3787. ISSN 0022-3263

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We applied a multicomponent approach to access a library of densely functionalized homo- and hetero-multivalent glycomimetics comprising aldehyde, amine and isocyanide components related to isopropylidene-protected D-fructose, L-sorbose, D-galactose and D-allose. Passerini products were obtained in very good yields (up to 78 %) and high diastereoselectivities (up to 98:2). Three types of products were obtained by the Ugi reaction; along with the “classical” four-component product - -acylaminoamides, a three-component -aminoamides and a four- component -aminoacylamides were isolated. Presence of multiple pathways is rationalized by the structure of imidate intermediate, mainly influenced by the amine component.

Item Type: Article
Uncontrolled Keywords: multicomponent reactions ; glycocomimetics
NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Project titleProject leaderProject codeProject type
Višekomponentne reakcije u sintezi peptidnih mimetika-MIMICRyIvanka JerićIP-2014-09-3102HRZZ
Depositing User: Ivanka Jerić
Date Deposited: 19 Nov 2021 13:50
DOI: 10.1021/acs.joc.9b03401

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