Stereoselective preparation of four 3-C-mannosylated d- and l-glucals from a single starting compound

Lövyova, Zuzana; Parkan, Kamil; Kniežo, L.

doi:10.1016/j.tet.2011.04.044

Cited by 6 publications

References 36 publications

(11 reference statements)

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Dihydropyrans by Cycloadditions of Oxadienes

et al. 2020

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3,4‐Dihydro‐2H‐pyrans are present in the skeletons of several natural products, and these versatile synthetic intermediates are readily transformed into tetrahydropyrans, pyridines, or 1,5‐dicarbonyl units. Among the strategies developed to access 3,4‐dihydro‐2H‐pyrans, the hetero‐Diels‐Alder reaction between an oxadiene and a dienophile is particularly valuable because up to three contiguous stereogenic centers can be created diastereo‐ and/or enantioselectively in a single step. This review addresses the mechanism of the reaction and presents methods for preparing the product dihydropyrans enantio‐ and diastereoselectively. Thermal and Lewis acid promoted cycloadditions are discussed, as is the role of activating groups on the oxadiene.

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Dihydropyrans by Cycloadditions of Oxadienes

et al. 2020

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Modular Stereoselective Synthesis of (1→2)‐C‐Glycosides based on the sp²–sp³ Suzuki–Miyaura Reaction

Oroszová

Choutka

Pohl

et al. 2015

Chemistry A European J

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This work reports a modular and rapid approach to the stereoselective synthesis of a variety of α- and β-(1→2)-linked C-disaccharides. The key step is a Ni-catalyzed cross-coupling reaction of D-glucal pinacol boronate with alkyl halide glycoside easily prepared from commercially available D-glucal. The products of this sp(2) -sp(3) cross-coupling reaction can be converted to glucopyranosyl, mannopyranosyl, or 2-deoxy-glucopyranosyl C-mannopyranosides by one- or two-step stereoselective oxidative-reductive transformations. To the best of our knowledge, we demonstrated the first synthetic application of a challenging sp(2) -sp(3) Suzuki-Miyaura cross-coupling reaction in carbohydrate chemistry.

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Nonhydrolyzable C-disaccharides, a new class of DC-SIGN ligands

Bertolotti

Oroszová

Sutkevičiūtė

et al. 2016

Carbohydrate Research

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Stereoselective preparation of four 3-C-mannosylated d- and l-glucals from a single starting compound

Cited by 6 publications

References 36 publications

Dihydropyrans by Cycloadditions of Oxadienes

Dihydropyrans by Cycloadditions of Oxadienes

Modular Stereoselective Synthesis of (1→2)‐C‐Glycosides based on the sp²–sp³ Suzuki–Miyaura Reaction

Nonhydrolyzable C-disaccharides, a new class of DC-SIGN ligands

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Stereoselective preparation of four 3-C-mannosylated d- and l-glucals from a single starting compound

Cited by 6 publications

References 36 publications

Dihydropyrans by Cycloadditions of Oxadienes

Dihydropyrans by Cycloadditions of Oxadienes

Modular Stereoselective Synthesis of (1→2)‐C‐Glycosides based on the sp2–sp3 Suzuki–Miyaura Reaction

Nonhydrolyzable C-disaccharides, a new class of DC-SIGN ligands

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Product

Resources

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Modular Stereoselective Synthesis of (1→2)‐C‐Glycosides based on the sp²–sp³ Suzuki–Miyaura Reaction