Table 2. The effect of a 3-O- and 6-O-acyl protection on the stereoselectivity of glucosylation a .
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Entry | Donor | Acceptor | Yield, α/β ratio |
1a | 30 |
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89%, 5.3/1 |
2a | 30 |
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93%, 11.2/1 |
3a | 31 |
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93%, 16.4/1 |
4b | 32 | 34 | 59%, 6.8/1 |
5c | 33 | 35 | 96%, 5.9/1 |
aConditions: aMeOTf, CH2Cl2, AW-300, –35 → –15 °C; bTf2O, DTBMP, CH2Cl2, –78 → 0 °C; cMeOTf, CH2Cl2, AW-300, 20 °C.