TABLE 5.
SN2 ring-opening products of epoxides derived from glycalsa
| entry | major product | |
|---|---|---|
| D-allal |
2 
|
30 
|
1 
|
31 
|
|
| D-gulal |
4 
|
32b 
|
6 
|
33c 
|
|
| 4-deoxy-glucal |
11 
|
34 
|
| 4-deoxy-allal |
3 
|
35 
|
| 3-deoxy-glucal |
9 
|
36d 
|
8 
|
37e 
|
|
| 3-deoxy-glucal |
15 
|
38 
|
14 
|
39f 
|
a
Relative stereochemistry of major products (facioselectivity ≥ 10:1, unless otherwise noted) confirmed by 1H NMR coupling constant analysis (see Table S1, Supporting Information).
b
3:2 ratio.
c
3:1 ratio.
d
1:1 ratio.
e
2:1 ratio.
f
4:1 ratio.