Supporting information for this article is available on the WWW thanks the Department of Energy (DE-FG0205ER15630) for their support.
thanks the Army Research Office for Staff Research Funding,Īnd M.R.G. US Army Research Office, Research Triangle Park, NC 27709 (USA) University of North Carolina at Chapel Hill Is high yielding in the presence of 1 mol % of 2+ Our efforts focused on the light-mediated conjugateĪddition of glycosyl radicals into acrolein (Scheme 2), which Photoredox methodology would provide the needed multigram quantities of 1. These goals therefore requiredĪ one-step scalable synthesis, and we envisioned that our Aldehydeġ can also enable the synthesis of C-linked glycosyl lipids by Vent the disadvantages of previous approaches. Planned synthesis of C-glycoconjugates from common aldehyde intermediate.
#Substitute for photoflow series
Recent advances in organocatalytic modification ofĪldehydes would enable the synthesis of a series of usefulĪmino acid derivatives from a single intermediate to circum. Intermediate for the divergent synthesis of C-glycoconjugate Photoredox-mediated methodology, could function as a key As a more efficient alternative, weĮnvisioned that aldehyde 1, accessible in one step fromĬommercial sources using our recently re ported visible-light Or the use of chiral starting materials (chiral auxiliaries orĪmino-acid-derived). Toxic reagents, harsh reaction conditions (strong acid or base), Methods require multiple synthetic steps, use expensive or Olefination/hydrogenation seuqences, addition of chiralĬarbon nucleophiles to glycosyl electrophiles, and organocatalytic amidation of aldehydes. The cross-metathesis of chiral alkenes, Ramberg–Bcklund Previously reported syntheses of C-glycopeptides include We report herein a highyielding and scalable approach to C-glycopeptides andĬ-glycolipids which utilizes a continuous (flow) photoredox Significant interest as a mild method of generating radicals Methods of C-glycoside synthesis through nickel-catalyzedĪnd photoredox processes. DespiteĮxtensive efforts, improved methods of C-glycoside synthesisĪre still in demand. Hydrolytic instability and thus extend bioavailability. The development of C-glycoside isosteres to overcome this Instability of the O-glycosidic linkage, which has stimulated
A common feature of glycoconjugates is the metabolic Vaccine therapeutics continue to drive investigations toĬharacterize the role of glycoconjugates in biological processes. These insights combined with their potential in Intercellular recognition events, such as immune response,Īnd along with glycolipids they help to form mammalian cell For example, glycoproteins are involved in Glycoconjugates are essential biological compounds having
Synthesis of C-Glycoamino Acids and C-Glycolipids** A Photoflow Reactor for the Continuous Photoredox-Mediated
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