Catalytic ceric ammonium nitrate mediated synthesis of 2-deoxy-1-thioglycosides
Paul, S; Jayaraman, N
| HERO ID | 3738347 |
|---|---|
| In Press | No |
| Year | 2004 |
| Title | Catalytic ceric ammonium nitrate mediated synthesis of 2-deoxy-1-thioglycosides |
| Authors | Paul, S; Jayaraman, N |
| Journal | Carbohydrate Research |
| Volume | 339 |
| Issue | 13 |
| Page Numbers | 2197-2204 |
| Abstract | Synthesis of 2-deoxy-1-thioglycosides from glycals, mediated by catalytic amounts of ceric ammonium nitrate is reported. Apart from the 2-deoxy-1-thioglycosides, formation of the 2,3-unsaturated enose, corresponding to the Ferrier product, is also observed, especially for the glucal substrates. A radical oxocarbenium ion and a thiolate intermediates are most likely to mediate the reaction. Upon synthesis of 2-deoxy-1-thioglycosides, few representative glycosylation reactions with both aglycosyl and glycosyl acceptors were performed and alpha-anomeric 2-deoxy glycosides were obtained exclusively. |
| Doi | 10.1016/j.carres.2004.07.010 |
| Pmid | 15337447 |
| Wosid | WOS:000223954900005 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |