Synthese von C-Glycosiden der N-Acetylneuraminsäure und weiteren Derivaten
Synthesis of C-Glycosides of N-Acetylneuraminic Acid and Other DerivativesReaction of the β-pyranosyl chloride 1 of N-acetylneuraminic acid with allyl(tributyl)stannane under radical-induced conditions affords a mixture of the allyl C-glycosides 2/3. After deprotection, the pure allyl α-C-glycoside 5 and the analogous β isomer 7 can be isolated. The allyl C-glycosides 2 and 3 are converted into the corresponding epoxypropyl C-glycosides 9 and 11 by epoxidation of the allylic group. Further modified allyl C-glycosides are prepared from the C-3-hydroxylated N-acetylneuraminic acid, which are available as pure α- and β-C-glycosides 19 and 21 after deprotection. At C-3 modified compounds are also synthesized which have allyl and azido residues at C-3. All compounds are interesting as potential inhibitors of sialidases, CMP sialate syntheses, and viral infection..
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
1991 |
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| Erschienen: |
1991 |
| Reproduktion: |
Wiley InterScience Backfile Collection 1832-2000 |
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| Enthalten in: |
Zur Gesamtaufnahme - volume:1991 |
| Enthalten in: |
Liebigs Annalen - 1991(1991) vom: Mai, Seite 487-495 |
| Sprache: |
Deutsch |
|---|
| Beteiligte Personen: |
Paulsen, Hans [Sonstige Person] |
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| Links: |
dx.doi.org [Deutschlandweit zugänglich] |
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| Umfang: |
9 |
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| Förderinstitution / Projekttitel: |
|
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| PPN (Katalog-ID): |
NLEJ162401191 |
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| 245 | 1 | 0 | |a Synthese von C-Glycosiden der N-Acetylneuraminsäure und weiteren Derivaten |
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| 520 | |a Synthesis of C-Glycosides of N-Acetylneuraminic Acid and Other DerivativesReaction of the β-pyranosyl chloride 1 of N-acetylneuraminic acid with allyl(tributyl)stannane under radical-induced conditions affords a mixture of the allyl C-glycosides 2/3. After deprotection, the pure allyl α-C-glycoside 5 and the analogous β isomer 7 can be isolated. The allyl C-glycosides 2 and 3 are converted into the corresponding epoxypropyl C-glycosides 9 and 11 by epoxidation of the allylic group. Further modified allyl C-glycosides are prepared from the C-3-hydroxylated N-acetylneuraminic acid, which are available as pure α- and β-C-glycosides 19 and 21 after deprotection. At C-3 modified compounds are also synthesized which have allyl and azido residues at C-3. All compounds are interesting as potential inhibitors of sialidases, CMP sialate syntheses, and viral infection. | ||
| 533 | |f Wiley InterScience Backfile Collection 1832-2000 | ||
| 700 | 1 | |a Paulsen, Hans |4 oth | |
| 700 | 1 | |a Matschulat, Peter |4 oth | |
| 773 | 0 | 8 | |i in |t Liebigs Annalen |d Weinheim : Wiley-VCH |g 1991(1991) vom: Mai, Seite 487-495 |w (DE-627)NLEJ159071070 |x 0947-3440 |7 nnns |
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