One-pot production of alkyl glycosidesa.
| Entry | Donor | Alcohol | Product | Isolated yield (%) |
|---|---|---|---|---|
| 1 | GlcNAc 2a | n-Pentenol |
|
73, 48b |
| 2 | GlcNAc 2a | Benzyl alcohol |
|
75 |
| 3 | GlcNAc 2a | Isopropanol |
|
76 |
| 4 | GlcNAc 2a | tert-Butanol |
|
45 |
| 5 | GalNAc 2b | Benzyl alcohol |
|
43 |
| 6 | ManNAc 2c | Benzyl alcohol |
|
57 |
Reaction conditions: (i) DMC, Et3N, H2O, 0 °C, 1 h, then freeze-dry; (ii) alcohol as solvent, TsOH (1 equiv.), 4 Å powdered molecular sieves, rt, 3 h.
Reaction performed in MeCN/DMF in the presence of 5 equiv. of alcohol as acceptor.