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Details van artikel 166 van 252 gevonden artikelen
| Titel: |
Synthesis and Reactions of C-Hetaryl Substituted Ketoses |
| Auteur: |
Streicher, Hansjorg Reiner, Martin Schmidt, Richard R. |
| Verschenen in: |
Journal of carbohydrate chemistry |
| Paginering: | Jaargang 16 (1997) nr. 3 pagina's 277-298 |
| Jaar: |
1997-03-01 |
| Inhoud: |
O-Benzyl protected gluconolactone 1 reacts readily with 2-lithio derivatives of quinaldine, 2-methylquinoxaline, 2-methylbenzimidazole and N-protected derivatives, and 1-benzyloxymethyl-2-methylimidazole at low temperatures to afford as monoaddition products the corresponding D-gluco-2-heptuloses 2-5. The benzyl protective groups can be readily removed by hydrogenolysis as shown for the transformation of 4a into 8. Acylation reactions with 4a exhibited an interesting interplay between O- and N-acylation which is dependent on the nature of the acylating agent and on the reaction conditions. Reductive removal of the anomeric hydroxy group in 4a-c and 5 was readily performed via elimination products 18a-c and 23; their hydrogenation with Pd/C gave directly the O,N-deprotected C-β-D-glucopyranosylmethyl derivatives 21 and 25, respectively. |
| Uitgever: |
Taylor & Francis |
| Bronbestand: |
Elektronische Wetenschappelijke Tijdschriften |
Details van artikel 166 van 252 gevonden artikelen
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