Synthesis of Pyrano- and Pyrido-Anellated Pyranosides as Precursors for Nucleoside Analogues
Thiele, G; Feist, H; Peseke, K
| HERO ID | 4933490 |
|---|---|
| In Press | No |
| Year | 2005 |
| Title | Synthesis of Pyrano- and Pyrido-Anellated Pyranosides as Precursors for Nucleoside Analogues |
| Authors | Thiele, G; Feist, H; Peseke, K |
| Journal | Journal of Carbohydrate Chemistry |
| Volume | 24 |
| Issue | 3 (Apr 2005) |
| Page Numbers | 209-218 |
| Abstract | The push-pull activated methyl (3Z)-4,6-O-benzylidene-3-[(methylthio)methylene]-3-deoxy-a-D-eryth ro-hexopy ranosid-2-ulose (1) reacted with dialkyl malonate in the presence of potassium carbonate to give the alkyl (2R,4aR,6S,10bS)-4a,6,8,10b-tetrahydro-6-methoxy-8-oxo-2-phenyl-4H -pyrano[3 ',2':4,5]pyrano[3,2-d][1,3]dioxine-9-carboxylates 2 and 3. Treatment of 1 with 3-oxo-N-phenyl-butyramide, N-(4-methoxy-phenyl)-3-oxo-butyramide, and 3-oxo-N-o-tolyl-butyramide, respectively, in the presence of potassium carbonate and 18-crown-6 yielded the (2R,4aR,6S,10bS)-9-acetyl-7-aryl-4,4a,7,10b-tetrahydro-6-methoxy-2 -phenyl[1 ,3]dioxino-[4',5':5,6]pyrano[3,4-b]pyridin-8(6H)-ones 4-6. (2R,4aR,6S,10bS)-4,4a,8,10b-Tetrahydro-6-methoxy-8-oxo-2-phenyl-4H -pyrano[3 ',2':4,5]pyrano[3,2-d][1,3]dioxine-9-carboxamide (7) was prepared by anellation reactions of 1 either with malononitrile or with cyanoacetamide. |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | potassium carbonate; nucleoside analogs; Carbohydrates |