Synthesis of C-glycosylated amino acids by hetero-Diels–Alder addition of ethyl 2-nitrosoacrylate to exo-glycals

C-Glycoamino acids bearing a variety of sugar moieties were prepared by the hetero-Diels–Alder addition of ethyl 2-nitrosoacrylate to exo-glycals. The reaction proceeds smoothly to yield spirocyclic oxazines that can be converted into useful products by several hydrogenolytic techniques.

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Bibliographische Detailangaben
Veröffentlicht in:	Carbohydrate research 2011-02, Vol.346 (2), p.230-237
Hauptverfasser:	Massen, Zoe S., Sarli, Vassiliki C., Coutouli-Argyropoulou, Evdoxia, Gallos, John K.
Format:	Artikel
Sprache:	eng
Schlagworte:	Acrylates - chemistry acrylic acid amino acid derivatives amino acids Amino Acids - chemical synthesis C-Glycosylated amino acids Catalytic hydrogenation Ethyl 2-nitrosoacrylate Ethyl bromopyruvate exo-Glycals glycosidic linkages Glycosylation Hetero-Diels–Alder cycloaddition heterocyclic compounds nitroso compounds Nitroso Compounds - chemistry sugars synthesis
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Beschreibung
Zusammenfassung:	C-Glycoamino acids bearing a variety of sugar moieties were prepared by the hetero-Diels–Alder addition of ethyl 2-nitrosoacrylate to exo-glycals. The reaction proceeds smoothly to yield spirocyclic oxazines that can be converted into useful products by several hydrogenolytic techniques.
ISSN:	0008-6215 1873-426X
DOI:	10.1016/j.carres.2010.12.001