Table 1.
Electrochemical oxidationa of 3α,5α-cyclocholestan-6β-yl ethers 6a–h in the presence of 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (7).
| Substrate 6 | 3β-O-(1’,2’:3’,4’-di-O-isopropylidene-D-galactopyranos-6’-yl)-cholest-5-ene (11) (yield) | Isomerization product 12 (yield) | Other steroidal product (yield) |
| 6a | 47% | 8%b | 2 (17), 14 (3%), 13 (2%) |
| 6b | 40% | 24% | 13 (2%), 1 (1%) |
| 6c | 51% | 45% | 13 (2%), 14 (1%) |
| 6d | 41% | 34% | 1 (2%), 2 (2%) |
| 6e | 50% | 40% | 1 (trace) |
| 6f | 58% | 22% | 1 (4%), 13 (1%), 14 (1%) |
| 6g | 9% | 12% | 15 (18%) |
| 6h | 52% | 1% | 13 (9%), 1 (6%), 2 (5%) |
aElectrochemical reaction conditions given in the Experimental section. bCompound 12a = 1 (cholesterol).