Kettenverlängerung von 1-Desoxy-l-Nitroalditolen durch Nitriloxid-Cycloaddition: Synthese von 4-N-Substituierten 3,4-Didesoxy-2-Ulosonsiiuren
Treatment of protected nitroalditols 1a or 2 with silylenolpyruvate (3) or methyl acrylate leads via nitrile oxide cycloaddition to cyclo-tautomers of oximes, 5 or 4, respectively 4,5-dihydro-isoxazole 6. N-Acetyl-4-deoxy-4-(EZ)-hydroxyimino-neuraminic acid (7) is obtained by deprotection of 4. Hydr...
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| Main Authors: | , |
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| Format: | Article (Journal) |
| Language: | German |
| Published: |
30 April 1998
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| In: |
Tetrahedron
Year: 1998, Volume: 54, Issue: 18, Pages: 4539-4560 |
| ISSN: | 1464-5416 |
| DOI: | 10.1016/S0040-4020(98)00168-9 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1016/S0040-4020(98)00168-9 Verlag, lizenzpflichtig, Volltext: https://www.sciencedirect.com/science/article/pii/S0040402098001689 
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| Author Notes: | Hans Mack und Reinhard Brossmer |
| Summary: | Treatment of protected nitroalditols 1a or 2 with silylenolpyruvate (3) or methyl acrylate leads via nitrile oxide cycloaddition to cyclo-tautomers of oximes, 5 or 4, respectively 4,5-dihydro-isoxazole 6. N-Acetyl-4-deoxy-4-(EZ)-hydroxyimino-neuraminic acid (7) is obtained by deprotection of 4. Hydrogenation of 7 yields N-acetyl-4-amino-4-deoxy-neuraminic acid (9) and pentahydroxy-nononic acids 12a,b. The synthesis is useful for the chain extension of protected nitroalditols 13a and 20a, to give the corresponding oximes 15 and 22. This work provides a general method for the extension of sugar chains by three C-atoms and thus a novel synthesis of α-keto acids containing an oxime and amino function. |
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| Item Description: | Elektronische Reproduktion der Druck-Ausgabe 15. April 1999 Gesehen am 24.06.2024 |
| Physical Description: | Online Resource |
| ISSN: | 1464-5416 |
| DOI: | 10.1016/S0040-4020(98)00168-9 |