Synthesis and use of new C-glycosyl bicyclic lactones

Listkowski, Arkadiusz; Otman, Otman; Chambert, Stéphane; Queneau, Yves

doi:10.1016/j.tetlet.2015.07.017

Cited by 2 publications

(1 citation statement)

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“…We postulated that compound 21 results from TFA promoted acetal removal followed by nucleophilic attack of O4 on carboxamide function. Few intramolecular lactonizations of C ‐glycosyl ester derivatives have already been described in the literature and led to the formation of C ‐glycosyl bicyclic lactones where the lactone ring is annulated to a furanoid or a pyranoide system. However, to the best of our knowledge, no lactonization of amide derivatives in such saccharidic systems has been described.…”

Section: Resultsmentioning

confidence: 99%

Sugar γ‐Amino Acids as Building Blocks for the Synthesis of Cyclic Neoglycopeptides.

et al. 2018

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Anomeric sugar γ‐amino acids efficiently obtained by nucleophilic addition of nitronate anion on sugar olefins are useful building blocks for the preparation of new cyclic glycopeptides. Cyclopeptides have interesting biological properties or find potential applications as templates for anchoring of a wide range of biomolecules or detection dyes. We report here the synthesis of two types of cyclic systems containing γ‐glyco amino acid and α‐amino acid units. A first example was prepared to demonstrate the feasibility of the cyclization of these original structures. To explore the feasibility with more functionalized structures, α‐amino acid and sugar amino‐acid moieties bearing additional functions were chosen as building blocks for the second macrocycle. Furthermore, we describe and explain some unexpected results obtained during deprotection of these new cyclic glycopeptides.

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Section: Resultsmentioning

confidence: 99%