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Application of the 2-deoxyglucose scaffold as a new chiral probe for elucidation of the absolute configuration of secondary alcohols.

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  • معلومة اضافية
    • المصدر:
      Publisher: Nature Publishing Group Country of Publication: England NLM ID: 101563288 Publication Model: Electronic Cited Medium: Internet ISSN: 2045-2322 (Electronic) Linking ISSN: 20452322 NLM ISO Abbreviation: Sci Rep Subsets: MEDLINE
    • بيانات النشر:
      Original Publication: London : Nature Publishing Group, copyright 2011-
    • الموضوع:
      Alcohols*/chemistry ; Deoxyglucose*; Carbon ; Glycosides/chemistry ; Molecular Conformation
    • نبذة مختصرة :
      Herein, we present the application of 2-deoxy-D-glucose derivatives as chiral probes for elucidation of the absolute configuration of chiral secondary alcohols. The probes are attached to the studied molecules via glycosylation reaction and the resulting products are examined by a set of standard 2D NMR experiments. The absolute configuration of an oxymethine carbon atom binding the probe is established on a basis of a set of diagnostic dipolar couplings (NOEs/ROEs). These correlations may be considered diagnostic due to a pronounced lack of conformational freedom of the formed glycosidic linkage. While the chance for an observation of the diagnostic signals is the highest when the resulting glycoside in an α-anomer. 2-deoxy-D-glucose was selected as a probe of choice since is it known to strongly prefer the formation of α-glycosides.
      (© 2022. The Author(s).)
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    • الرقم المعرف:
      0 (Alcohols)
      0 (Glycosides)
      7440-44-0 (Carbon)
      9G2MP84A8W (Deoxyglucose)
    • الموضوع:
      Date Created: 20221007 Date Completed: 20221011 Latest Revision: 20240905
    • الموضوع:
      20240905
    • الرقم المعرف:
      PMC9547072
    • الرقم المعرف:
      10.1038/s41598-022-21174-8
    • الرقم المعرف:
      36207399