Synthesis of the deculopyranosonic acid analog of N-acetylneuraminic acid, its 5-epimer and 6-epimer, and of 5-acetamido-1,3,5-trideoxy-d-glycero-d-galactonon-2-ulopyranose
Condensation of 2-acetamido-2-deoxy-5,6-O-isopropylidene-d-mannofuranose with disodium acetonedicarboxylate and subsequent esterification with diphenyldiazomethane yielded diphenylmethyl 6-acetamido-2,4,6-trideoxy-d-glycero-β-d-galacto-dec-3-ulopyranosonate (3), and its 5- and 6-epimer. Hydrogenatio...
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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
15 December 1992
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| In: |
Carbohydrate research
Year: 1992, Volume: 236, Pages: 89-96 |
| ISSN: | 1873-426X |
| DOI: | 10.1016/0008-6215(92)85008-N |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1016/0008-6215(92)85008-N Verlag, lizenzpflichtig, Volltext: https://www.sciencedirect.com/science/article/pii/000862159285008N 
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| Author Notes: | Heinz-Werner Hagedorn, Hans Merten, Reinhard Brossmer |
| Summary: | Condensation of 2-acetamido-2-deoxy-5,6-O-isopropylidene-d-mannofuranose with disodium acetonedicarboxylate and subsequent esterification with diphenyldiazomethane yielded diphenylmethyl 6-acetamido-2,4,6-trideoxy-d-glycero-β-d-galacto-dec-3-ulopyranosonate (3), and its 5- and 6-epimer. Hydrogenation gave the corresponding free acids. Hydrogenation of ester 3 and working-up under alkaline conditions afforded stable ammonium 6-acetamido-2,4,6-trideoxy-d-glycero-β-d-galacto-dec-3-ulopyranosonate which, on heating, led to an anomeric mixture of 5-acetamido-1,3,5-trideoxy-d-glycero-d-galacto-non-2-ulopyranose. |
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| Item Description: | Elektronische Reproduktion der Druck-Ausgabe 26. März 2001 Gesehen am 24.06.2024 |
| Physical Description: | Online Resource |
| ISSN: | 1873-426X |
| DOI: | 10.1016/0008-6215(92)85008-N |