Synthesis of monoglycosides, bisglycosides and open-chain ketoacetals from sugar derived exocyclic enol ethers

Das, Soumendra Nath; K, Praveen Krishna; Mandal, Sukhendu

doi:10.1039/c4ra03340j

Cited by 1 publication

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References 38 publications

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“…Mandal 60 synthesized glycosyl 1-benzopyran-2-imines (iminocoumarins) 141 via a one-pot, Cu-catalyzed, three-component reaction of sugar alkynes 137 , salicylaldehydes 138 , and sulfonyl azides 139 via a ketenimine intermediate formation (Scheme 36 ). This reaction used copper iodide (10 mol%) as the catalyst and triethylamine (2 equiv) as the base and gave various glycosyl 1-benzopyran-2-imines 141 in good yields (up to 88%).…”

Section: Synthesis Of Various Functionalized Sugar Compoundsmentioning

confidence: 99%

Sugars in Multicomponent Reactions: A Toolbox for Diversity-Oriented Synthesis

et al. 2023

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Multicomponent reactions (MCRs) cover strategically employed chemical transformations that incorporate three or more reactants in one pot leading to a functionalized final product. Thus, it is an ideal tool to achieve high levels of complexity, diversity, yields of desired products, atom economy, and reduced reaction times. Sugars belong to the class of naturally occurring compounds with fascinating applications in the field of drug discovery due to the presence of various hydroxy groups and well-defined stereochemistry. However, their potential in MCRs has been realized only recently. This account describes recent advances in the synthesis of sugar-derived heterocycles synthesized by MCRs. We hope to encourage the synthetic and medicinal chemistry community to apply this powerful MCR chemistry to generate novel glycoconjugate challenges.1 Introduction2 Synthesis of Various Functionalized Sugar Compounds2.1 Passerini and Ugi Multicomponent Reactions2.2 Petasis Reaction2.3 Hantzsch Reaction2.4 Domino Ferrier–Povarov Reaction2.5 Marckwald Reaction2.6 Groebke–Blackburn–Bienaymé (GBB) Reaction2.7 Prins–Ritter Reaction2.8 Debus–Radziszewski Imidazole Synthesis Reaction2.9 Mannich Reaction2.10 A3-Coupling Reaction2.11 [3+2]-Cycloaddition Reactions2.12 Miscellaneous Reactions3 Conclusion

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Section: Synthesis Of Various Functionalized Sugar Compoundsmentioning

confidence: 99%