Synthesis of new C-glycosyl aza-β3-amino acids building blocks

Andreini, Manuel; Felten, Anne‐Sophie; Thien, Hoang-Trang Tran; Taillefumier, Claude; Pellegrini‐Moise, Nadia; Chapleur, Yves

doi:10.1016/j.tetlet.2012.03.072

Cited by 4 publications

(1 citation statement)

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“…Aza‐β 3 ‐amino acids are peptidomimetics closely related to peptoids with the side chain attached on nitrogen but not the nitrogen of the amide group. To enlarge the field of glycopeptide mimics, Chapleur and co‐workers developed access to C ‐glycosylated N β ‐protected aza‐β 3 ‐amino acid building blocks from C ‐glycosyl aldehydes of gluco or galacto configuration 67 . N ‐Cbz‐β‐alanine hydrazide ( 83 ), prepared from β‐alanine, was treated with a sugar aldehyde derivative to give hydrazone 84 (Scheme ).…”

Section: Miscellaneousmentioning

confidence: 99%

From Glycopeptides to Glycopeptoids

Szekely¹,

Roy²,

Faure³

et al. 2014

Eur J Org Chem

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This review covers the published literature describing the synthesis of glycopeptoids, a family of glycopeptide mimics. Members of this family are composed of an N‐substituted glycine or β‐alanine oligomer backbone linked to one or several carbohydrate moieties at the amide nitrogen atoms. The interest in this class of biomimetics lies in their enhanced proteolytic stability and greater conformational flexibility relative to glycopeptides. This Microreview not only describes the different methods for synthesising glycopeptoids but also discusses their application both as glycopeptidomimetics and glycocluster constructs.

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Section: Miscellaneousmentioning

confidence: 99%

From Glycopeptides to Glycopeptoids

Szekely¹,

Roy²,

Faure³

et al. 2014

Eur J Org Chem

Self Cite

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Convenient Synthesis of 3‐Glycosylated Isocoumarins

Sudarshan

Aidhen

2016

Eur J Org Chem

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A new route for the synthesis of 3‐substituted and 8‐hydroxy‐3‐substituted isocoumarins was developed by modified Julia olefination for initial C–C bond formation between aldehydes and benzylic sulfones. Palladium‐catalyzed Meinwald rearrangement was used as a key step for the obtainment of ketone intermediates, which – upon base‐promoted intramolecular cyclization – afforded the desired isocoumarins. The developed method paves the way to hitherto unknown 3‐glycosylisocoumarins, in general, and 3‐glucosylisocoumarins, in particular, wherein the glucosyl moiety is attached to the pyrone ring of the isocoumarin framework.

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