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Optimization for synthesis of 3-tosylamino-2,3-dideoxyneoglycoconjugate 4a.
 | |||||
| Entry | Catalyst (mol %) | Solvent | Temperature (°C) | Time (h) | Yield (mol %)a |
| 1 | none | DMF | 100 | 20 | NRb |
| 2 | none | MeCN/H2O | 100 | 20 | NRb |
| 3 | none | MeOH | 100 | 20 | NRb |
| 4 | CuI (10) | THF | 60 | 12 | trace |
| 5 | CuSO4·5H2O (1) | t-BuOH/H2O | 70 | 20 | 46 |
| 6 | CuSO4·5H2O (1) | DMF | 70 | 12 | 97 |
| 7 | CuSO4·5H2O (1) | DMF | 70c | 0.25 | 98 |
aIsolated yield after purification. bNR = no reaction. cAssisted by microwave irradiation, 200 W.
