Glycal Derivatives

Priebe, Waldemar; Fokt, Izabela; Grynkiewicz, Grzegorz

doi:10.1007/978-3-540-30429-6_15

Cited by 12 publications

(16 citation statements)

References 221 publications

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“…29 Inspired by the results from Xiong and Ye 21,30 on the photocatalyzed trifluoromethylation of glycals which are reported to afford 2-trifluoromethyl-substituted glycals, we began our initial investigation on 2acetoxyglycals. 31 We decided to explore the possibility of obtaining C-perfluoroalkylated glycosyl compounds, by treatment 2-acetoxyglycals with commercially-available fluoroalkyl iodides under visible light photocatalysis. Fluoroalkyl iodides having 1, 4 and 6 carbon atoms were used.…”

Section: Scheme 1 Approaches To Fluoroalkylation Of Glycalsmentioning

confidence: 99%

Photocatalyzed reductive fluoroalkylation of 2-acetoxyglycals towards the stereoselective synthesis of α-1-fluoroalkyl-C-glycosyl derivatives

2020

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Section: Scheme 1 Approaches To Fluoroalkylation Of Glycalsmentioning

confidence: 99%

Photocatalyzed reductive fluoroalkylation of 2-acetoxyglycals towards the stereoselective synthesis of α-1-fluoroalkyl-C-glycosyl derivatives

2020

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“…Monosaccharides featuring a carbon-carbon double bond are valuable intermediates in organic synthesis. [1,2] These unsaturated sugars provide straightforward access to a variety of glycoside derivatives as well as enantiomerically pure highly functionalized non-carbohydrate products. For example, glycals, the widest and most studied family of unsaturated monosaccharides, are extensively employed as glycosylating agents in the preparation of 2-deoxy sugars and complex oligosaccharides, [3][4][5][6] and represent important precursors for the synthesis of C-glycosides.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Radical Reactions of Unsaturated Sugars

Goti

2022

ChemCatChem

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The functionalization of unsaturated carbohydrates is a powerful approach for the synthesis of a variety of glycoside derivatives, sugar mimics, and enantiomerically pure molecules. This Review will discuss recently developed catalytic radical methods for the functionalization of glycals, exo-glycals, and exo-enes, highlighting the opportunities they offer for new reaction design. While providing new routes for the synthesis of complex carbohydrates, catalytic radical transformations of unsaturated sugars overcome the limitations that typically affect classical protocols, such as the use of stoichiometric oxidants/reductants and hazardous and toxic reagents. Currently unaddressed challenges will also be discussed, suggesting new directions for future work and fostering new methodological developments and applications in the field.

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“…Glycals are a class of versatile chiral building blocks that have been extensively used in the synthesis of oligosaccharides and other biologically important molecules. 10,11 Although considerable effort has been devoted to developing a practical synthetic methodology for glycals, several serious issues persist in the currently available protocols, including the use of a toxic and excessive amount of reducing metal, poor generality, and the complicated preparation of the corresponding appropriate precursor (Fig. S1†).…”

Section: Introductionmentioning

confidence: 99%