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Rapid synthesis of carbohydrate derivatives, including mimetics of C-linked disaccharides and C-linked aza disaccharides, using the hetero-Diels-Alder reaction

Burland, Peter A ; Coisson, David ; Osborn, Helen M I

The Journal of organic chemistry, 05 November 2010, Vol.75(21), pp.7210-8 [Peer Reviewed Journal]

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  • Title:
    Rapid synthesis of carbohydrate derivatives, including mimetics of C-linked disaccharides and C-linked aza disaccharides, using the hetero-Diels-Alder reaction
  • Author: Burland, Peter A ; Coisson, David ; Osborn, Helen M I
  • Subjects: Aza Compounds -- Chemistry ; Biomimetic Materials -- Chemical Synthesis ; Carbon -- Chemistry ; Disaccharides -- Chemical Synthesis
  • Is Part Of: The Journal of organic chemistry, 05 November 2010, Vol.75(21), pp.7210-8
  • Description: In this work we demonstrate the value of performing a hetero-Diels-Alder reaction (HDAR) between Danishefsky's diene and a range of aldehydes or imines, under microwave irradiation. By using a range of aldehydes and imines, including those derived from carbohydrates, access to functionalized 2,3-dihydro-4H-pyran-4-ones or 2,3-dihydro-4-pyridinones in good to excellent synthetic yields is possible. A particular strength of the methodology is its ability to access mimetics of C-linked disaccharides and C-linked aza disaccharides, targets of current therapeutic interest, in a rapid, convenient, and diastereoselective manner. The effect of high pressure on the HDARs involving carbohydrate-derived aldehydes and imines is also explored, with enhancement in yields occurring for the aldehyde substrates. Finally, HDARs using carbohydrate derived ketones, enones, and enals are described under a range of conditions. Optimum results were obtained under high-pressure conditions, with highly functionalized carbohydrate derivatives being afforded, in good yields, in this way.
  • Language: English
  • Identifier: E-ISSN: 1520-6904 ; PMID: 20939521 Version:1 ; DOI: 10.1021/jo101219w

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