Table 1.
Optimization of Disaccharide 15
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---|---|---|---|---|
entry | donor/acceptor | scavenger | temp | yield (α-only) |
1a | 2:1 | TTBP | rt | 14%b |
2a | 2:1 | TTBP | 0 °C | 44%b |
3a | 2:1 | DTBMP | 0 °C | 11%b |
4c | 2:1 | TTBP | 0 °C | 18%b |
5d | 1:2 | TTBP | 0 °C | 47%b |
6d | 1:3 | TTBP | 0 °C | 64%b |
7d | 1:3 | TTBP | −10 °C | 74%e |
8d,f | 1:3 | TTBP | −10 °C | 69%e |
TCE/CH2Cl2 (2.7:1).
NMR yield, product identified in a complex with α,α-trehalose.
TCE/CH2Cl2/THF (6.5:1:3.2).
TCE/CH2Cl2 (1.6:1).
Isolated yield.
300 mg scale of 8.