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Tin Lewis acids are key in glycosylation. This study uses 119Sn NMR and DFT to show tin promoters form ion pairs with glycosyl donors, clarifying their role in reactions and anomerization.

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Area of Science:

  • Carbohydrate Chemistry
  • Organometallic Chemistry
  • Computational Chemistry

Background:

  • Tin-based Lewis acids are crucial catalysts in glycosylation reactions.
  • The exact mechanism of tin promoters in these transformations remains unclear.
  • Understanding tin's role is vital for developing efficient synthetic strategies.

Purpose of the Study:

  • To elucidate the mechanistic role of Sn(IV) promoters in glycosylation.
  • To investigate the interaction between tin promoters and glycosyl donors.
  • To clarify the influence of tin on anomerization processes.

Main Methods:

  • 119Sn Nuclear Magnetic Resonance (NMR) spectroscopy to probe tin species.
  • Density Functional Theory (DFT) calculations to model reaction pathways.
  • Comparison of experimental and computed 119Sn chemical shifts for structural validation.

Main Results:

  • Evidence for the formation of stable ion pairs between glycosyl oxocarbenium ions and tin counterions.
  • 119Sn NMR chemical shifts confirm the coordination environment of tin species.
  • DFT calculations support a detailed mechanism for anomerization involving C-O bond cleavage and rotation.

Conclusions:

  • Tin promoters actively participate in glycosylation by forming ion pairs with key intermediates.
  • The study provides structural insights into tin coordination during the reaction.
  • A refined mechanism for tin-mediated anomerization is proposed, aiding Lewis acid design.