Table 1. Glycosylation between 2-Azido Glu/Gal Donors and 4-OH-2-azido Glu/Gal Acceptors.
| entry | donor | acceptor | conc (mmol/mL) | additive | equiv | T (°C) | product | yield (%)a | α:βb |
|---|---|---|---|---|---|---|---|---|---|
| 1 | 1 | 4 | 0.1 | DMF | 16 | 0 | 8 | 32 | >20:1 |
| 2 | 1 | 4 | 0.1 | DMF | 16 | rt | 8 | 38 | >20:1 |
| 3 | 1 | 4 | 0.1 | NFM | 16 | rt | 8 | 55 | >20:1 |
| 4 | 1 | 4 | 0.1 | MPF | 16 | 0 | 8 | 91 | ∼15:1 |
| 5 | 2 | 5 | 0.1 | DMF | 16 | 0 | 8 | 23 | 6:1 |
| 6 | 2 | 5 | 0.1 | NFM | 16 | 0 | 9 | 24 | 6:1 |
| 7 | 2 | 5 | 0.1 | MPF | 16 | 0 | 9 | 83 | 5:1 |
| 8 | 2 | 5 | 0.1 | MPF | 16 | –10 | 9 | 43 | 10:1 |
| 9 | 2 | 5 | 0.2 | MPF | 16 | –10 | 9 | 88 | 10:1 |
| 10 | 3 | 6 | 0.1 | MPF | 16 | –10 | 10 | 88 | 8:1 |
| 11 | 3 | 7 | 0.1 | MPF | 16 | –10 | 11 | 80 | 4:1 |
a
Isolated yield.
b
The α:β ratio was determined by 1H NMR.