Table 1.
Entry | Acceptor | Product | % Yield, α:β ratio | 3JCH (Hz) |
---|---|---|---|---|
1 | BnOH |
30 |
96%, α-only | 30: 7.2 |
2 |
27 |
31αβ |
87%, 6.7:1 | 31α: 6.4 |
3 |
26 |
32α,β |
82%, 4.4:1 | 32α: 6.9 |
4 |
28 |
33α,β |
75%, a4.5:1 |
33α: 7.2 33β: 0 |
5 |
29 |
34α,β |
88%, 34α:34β:35α= 4.7:1:0.9 | 34α: 7.0 |
35 |
35α: 6,3 | |||
6 | 1-adamantanol |
36α,β |
73%, 4.2:1 | 36α: 5.7 |
Glycosylation gave an 84% yield of an inseparable 4.5:1 α:β mixture of the disaccharides, which was saponified to give the products 33α and 33β.