Santana, Andres G.; Montalvillo-Jimenez, Laura; Diaz-Casado, Laura; Mann, Enrique; Jimenez-Barbero, Jesus; Gomez, Ana M.; Asensio, Juan Luis published the artcile< Single-Step Glycosylations with 13C-Labelled Sulfoxide Donors: A Low-Temperature NMR Cartography of the Distinguishing Mechanistic Intermediates>, Related Products of 4064-06-6, the main research area is NMR glycosylation cartog glycosyl sulfoxide donor intermediate detection monitoring; NMR spectroscopy; carbohydrates; glycosylation; isotopic labelling; reaction mechanisms.
Glycosyl sulfoxides have gained recognition in the total synthesis of complex oligosaccharides and as model substrates for dissecting the mechanisms involved. Reactions of these donors are usually performed under pre-activation conditions, but an exptl. more convenient single-step protocol has also been reported, whereby activation is performed in the presence of the acceptor alc.; yet, the nature and prevalence of the reaction intermediates formed in this more complex scenario have comparatively received minimal attention. Herein, a systematic NMR-based study employing both 13C-labeled and unlabeled glycosyl sulfoxide donors for the detection and monitoring of marginally populated intermediates is reported. The results conclusively show that glycosyl triflates play a key role in these glycosylations despite the presence of the acceptor alc. Importantly, the formation of covalent donor/acceptor sulfonium adducts was identified as the main competing reaction, and thus a non-productive consumption of the acceptor that could limit the reaction yield was revealed.
Chemistry – A European Journal published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Related Products of 4064-06-6.
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts