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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Abstract
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 | ||||||||
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| Uncontrolled Keywords: | multicomponent reactions ; glycocomimetics | ||||||||
| Subjects: | NATURAL SCIENCES NATURAL SCIENCES > Chemistry > Organic Chemistry |
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| Divisions: | Division of Organic Chemistry and Biochemistry | ||||||||
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| Depositing User: | Ivanka Jerić | ||||||||
| Date Deposited: | 19 Nov 2021 13:50 | ||||||||
| URI: | http://fulir.irb.hr/id/eprint/6755 | ||||||||
| DOI: | 10.1021/acs.joc.9b03401 |
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