Novel autoxidation and Michael addition of a butenolide-containing sugar leading to a C-branched-chain glucopyranosidulose, and X-ray structure of intermediates
Liu, HM; Zhang, F; Zhang, J; Li, S
| HERO ID | 4923640 |
|---|---|
| In Press | No |
| Year | 2003 |
| Title | Novel autoxidation and Michael addition of a butenolide-containing sugar leading to a C-branched-chain glucopyranosidulose, and X-ray structure of intermediates |
| Authors | Liu, HM; Zhang, F; Zhang, J; Li, S |
| Journal | Carbohydrate Research |
| Volume | 338 |
| Issue | 17 |
| Page Numbers | 1737-1743 |
| Abstract | A butenolide-containing sugar available from the aldol condensation of methyl 4,6-O-benzylidene-alpha-D-glucopyranosid-2-ulose with diethyl malonate is autoxidized at the C-3 position into the corresponding alpha,beta-unsaturated gamma-lactone sugar by air, which subsequently undergoes 1,4-conjugate (Michael) addition of hydroxide ion (or water) leading to a C-branched-chain glucopyranosidulose. The autoxidations are also performed in weakly basic, neutral and weakly acidic medium, respectively. |
| Doi | 10.1016/S0008-6215(03)00257-X |
| Pmid | 12892940 |
| Wosid | WOS:000184716600004 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |
| Keyword | butenolide-containing sugar; 2-oxoglucopyranoside; autoxidation |