C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction.
Int J Mol Sci
; 20(24)2019 Dec 10.
Article
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| MEDLINE
| ID: mdl-31835639
ABSTRACT
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 9010 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.
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01-internacional
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MEDLINE
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En
Revista:
Int J Mol Sci
Año:
2019
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Article
País de afiliación:
Croacia