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UV-mediated anomeric activation.

Niklas Henrik Fischer1, Alicja Klaudia Bałuta2, Maciej Tadeusz Szpak2

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UV light activates glycosyl trichloroacetimidates (TCAs) to form glycosyl chlorides or O-glycosides. Solvent choice dictates product formation, with acetonitrile favoring O-glycosylation and other solvents yielding chlorides.

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Area of Science:

  • Organic Chemistry
  • Carbohydrate Chemistry
  • Photochemistry

Background:

  • Glycosyl trichloroacetimidates (TCAs) are versatile intermediates in carbohydrate synthesis.
  • Efficient methods for activating TCAs are crucial for accessing diverse glycosylated products.

Purpose of the Study:

  • To investigate the UV-mediated activation of glycosyl TCAs.
  • To determine the influence of solvent and substrate structure on product formation.
  • To elucidate the mechanism of byproduct formation.

Main Methods:

  • Photochemical activation of various glycosyl TCAs using UV light.
  • Systematic variation of solvents (THF, Et2O, CH2Cl2, acetonitrile) and protecting groups.
  • Analysis of reaction products using spectroscopic techniques.

Main Results:

  • UV irradiation of glycosyl TCAs yielded glycosyl α-chlorides in ethereal solvents and dichloromethane.
  • In acetonitrile, O-glycosylation occurred with excess alcohols.
  • A per-acetylated glucosyl TCA reacted with THF to form a 4'-chlorobutyl β-glucoside.
  • Fluorescent byproducts were observed with benzyl-protected TCAs and in ethereal solvents.

Conclusions:

  • UV-mediated activation provides a tunable method for synthesizing glycosyl chlorides and O-glycosides.
  • Solvent selection is critical for directing the outcome of TCA activation.
  • Radical decomposition pathways may contribute to byproduct formation.