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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| Veröffentlicht in: | Carbohydrate research 2011-02, Vol.346 (2), p.230-237 |
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| container_issue | 2 |
| container_start_page | 230 |
| container_title | Carbohydrate research |
| container_volume | 346 |
| creator | Massen, Zoe S. Sarli, Vassiliki C. Coutouli-Argyropoulou, Evdoxia Gallos, John K. |
| description | 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. |
| doi_str_mv | 10.1016/j.carres.2010.12.001 |
| format | Article |
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| fulltext | fulltext |
| identifier | ISSN: 0008-6215 |
| ispartof | Carbohydrate research, 2011-02, Vol.346 (2), p.230-237 |
| issn | 0008-6215 1873-426X |
| language | eng |
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| source | Elsevier ScienceDirect Journals Complete - AutoHoldings; MEDLINE |
| subjects | 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 |
| title | Synthesis of C-glycosylated amino acids by hetero-Diels–Alder addition of ethyl 2-nitrosoacrylate to exo-glycals |
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