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 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.
Highlights
Carbohydrates are a ubiquitous group of natural products that mediate numerous, highly diverse cellular events and, participate in development of various diseases
In an endeavor to provide an efficient route to glycomimetics comprising structurally diverse carbohydrate units, we describe a robust, stereoselective, multicomponent approach
As a part of our ongoing project aimed to enrich the chemical space of natural product-like compounds, we have recently reported a strategy to access a library of densely functionalized glycomimetics
Summary
Carbohydrates are a ubiquitous group of natural products that mediate numerous, highly diverse cellular events and, participate in development of various diseases. Synthetic carbohydrates and their derivatives are powerful tools in biology and medicinal chemistry with diverse applications ranging from diagnostics to vaccines and therapeutics [1,2,3,4]. For the first time, bis-isopropylidene-protected d-fructose-derived aldehyde 1 (Figure 1) in the Passerini reaction with various acids and isocyanides [12]. Carbohydrate-derived aldehydes were reported to affect diastereoselectivity in multicomponent reactions (MCRs), observed stereoselectivity was highly influenced by OH-protecting groups (acetyl or benzyl protecting groups were frequently used) and other components in MCRs [13]. To complement our selection of carbohydrate-related carbonyl components, two ketones were envisaged: derivatives 8 and 9, obtained from 1,2:5,6-di-O-isopropylidene-α-d-glucofuranose and 1,2:4,5-di-O-isopropylidene-β-d-fructopyranose, respectively (Figure 1)
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
