Facile Cu(OTf)2-catalyzed preparation of per-O-acetylated hexopyranoses with stoichiometric acetic anhydride and sequential one-pot anomeric substitution to thioglycosides under solvent-free conditions
Tai, CA; Kulkarni, SS; Hung, SC
| HERO ID | 5417741 |
|---|---|
| In Press | No |
| Year | 2003 |
| Title | Facile Cu(OTf)2-catalyzed preparation of per-O-acetylated hexopyranoses with stoichiometric acetic anhydride and sequential one-pot anomeric substitution to thioglycosides under solvent-free conditions |
| Authors | Tai, CA; Kulkarni, SS; Hung, SC |
| Journal | Journal of Organic Chemistry |
| Volume | 68 |
| Issue | 22 |
| Page Numbers | 8719-8722 |
| Abstract | Solvent-free per-O-acetylation of hexoses with a stoichiometric amount of acetic anhydride employing 0.03 mol % Cu(OTf)2 proceeded in high yields (90-99%) at room temperature to give exclusively pyranosyl products as an anomeric mixture, the alpha/beta ratio of which was dependent on the temperature and amount of catalyst used. Sequential anomeric substitution with p-thiocresol in the presence of BF3.etherate gave the thioglycosides, isolated exclusively or predominantly as one anomer in 66-75% yields. |
| Doi | 10.1021/jo030073b |
| Pmid | 14575510 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |