Palladium−Charcoal-Catalyzed Reduction of Tri-O-acetyl-β-l -Fucopyranosyl Cyanide: A Route to Small Cluster Oligosaccharide Mimetics (SCOMs)
| Autor: | Paul H. Gross, Chang-Nan Chen, Patrick R. Jones, Pasit Phiasivongsa, Julie Gallagher, Vyacheslav V. Samoshin |
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| Rok vydání: | 2002 |
| Předmět: |
chemistry.chemical_classification
Cyanides Carbamoyl chloride Cyanide Molecular Mimicry Organic Chemistry Synthon Oligosaccharides chemistry.chemical_element Oligosaccharide Biochemistry Combinatorial chemistry Catalysis chemistry.chemical_compound chemistry Charcoal Organic chemistry Amine gas treating Glycosyl Physical and Theoretical Chemistry Oxidation-Reduction Palladium Fucose |
| Zdroj: | Organic Letters. 4:4587-4590 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol020123j |
| Popis: | [reaction: see text] Synthesis of glycosyl cyanides was optimized with a new catalyst system. Reduction of tri-O-acetyl-beta-L-fucopyranosyl cyanide with Pd-hydrogen, in the presence of Ac(2)O and Boc(2)O, gave N-protected-mono- and -di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl)-amines, which allow for the syntheses of small cluster oligosaccharide mimetics of fucopyranosylomethyl-substituted ureas. From di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl) amine was also prepared a carbamoyl chloride as a potentially useful synthon for preparation of more complex C-glycosidic conjugates. |
| Databáze: | OpenAIRE |
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