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C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction

Vlahoviček-Kahlina, Kristina; Suć Sajko, Josipa; Jerić, Ivanka (2019) C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction. International journal of molecular sciences, 20 (24). ISSN 1422-0067

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Carbohydrates and their conjugates are the most abundant natural products, with diverse and highly important biological roles. Synthetic glycoconjugates are versatile tools used to probe biological systems and interfere with them. In an endeavor to provide an efficient route to glycomimetics comprising structurally diverse carbohydrate units, we describe herein a robust, stereoselective, multicomponent approach. Isopropylidene-protected carbohydrate- derived aldehydes and ketones were utilized in the Passerini reaction, giving different glycosylated structures in high yields and diastereoselectivities up to 90:10 diastereomeric ratio (d.r). Access to highly valuable building blocks based on α-hydroxy C- glycosyl acids or more complex systems was elaborated by simple post-condensation methodologies

Item Type: Article
Uncontrolled Keywords: multicomponent reactions ; carbohydrates ; diastereoselective synthesis ; glycosylation ; C-glycosides
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Depositing User: Ivanka Jerić
Date Deposited: 08 Dec 2020 14:46
DOI: 10.3390/ijms20246236

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