Synthesis and reactions of c-hetaryl substituted ketoses
Streicher, H; Reiner, M; Schmidt, RR
| HERO ID | 4940977 |
|---|---|
| In Press | No |
| Year | 1997 |
| Title | Synthesis and reactions of c-hetaryl substituted ketoses |
| Authors | Streicher, H; Reiner, M; Schmidt, RR |
| Journal | Journal of Carbohydrate Chemistry |
| Volume | 16 |
| Issue | 3 |
| Page Numbers | 277-298 |
| Abstract | 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-beta-D-glucopyranosylmethyl derivatives 21 and 25, respectively. |
| Doi | 10.1080/07328309708006530 |
| Wosid | WOS:A1997WX88300002 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |