Synthese von 6-Thiosialinsäuren
The synthesis of 2-acetamido-2-deoxy-3-thio-d-mannose (11) is described. Chain elongation of thiazoline 10 with potassium-di-O-tbutyl-oxaloacetate yields epimeric 6-thiosialic acids 14 and 15. Chain extension of 18 with oxaloacetate/Ni++ results in the formation of N-acetyl-6-thioneuraminic acid (21...
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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: 4521-4538 |
| ISSN: | 1464-5416 |
| DOI: | 10.1016/S0040-4020(98)00167-7 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1016/S0040-4020(98)00167-7 Verlag, lizenzpflichtig, Volltext: https://www.sciencedirect.com/science/article/pii/S0040402098001677 
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| Author Notes: | Hans Mack, Reinhard Brossmer |
| Summary: | The synthesis of 2-acetamido-2-deoxy-3-thio-d-mannose (11) is described. Chain elongation of thiazoline 10 with potassium-di-O-tbutyl-oxaloacetate yields epimeric 6-thiosialic acids 14 and 15. Chain extension of 18 with oxaloacetate/Ni++ results in the formation of N-acetyl-6-thioneuraminic acid (21). Starting from 21 synthesis of α-azide 25 and dehydro-compound 27 was accomplished by treatment of 23 with sodium azide. On the other hand lewis acid catalyzed azidation of 22β with azidotrimethylsilane afforded β-azide 29. |
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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)00167-7 |