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Effect of Catalysts on Pyrophsophate Formation via Scheme 3
| Entry | 8 | Catalyst (4 eq) | pKa (H2O) | Time (d) | Yield of 10 (%) |
|---|---|---|---|---|---|
| 1 | 8a | - | - | 7 | 69 |
| 2 | 8a | Et3N·HCl | 10.8 | 7 | 71 |
| 3 | 8a | DMAP·HCl | 9.2 | 1 | 69 |
| 4 | 8a | Imidazole·HCl | 7.0 | 1 | 75 |
| 5 | 8a | N-Mehylimidazole HCl | 7.1 | 0.5 | 77 |
| 6 | 8a | N-Mehylimidazole HOTf | 7.1 | 0.5 | 72 |
| 7 | 8a | Pyridine·HCl | 5.2 | 0.5 | 75 |
| 8 | 8a | Pyridine·HOTf | 5.2 | 0.5 | 68 |
| 9 | 8a | Tetrazole | 4.9 | 1 | 63 |
| 10 | 8b | N-Mehylimidazole HCl | 7.1 | 0.5 | 54 |
Yields were determined after removal of protecting groups.
