Photochemical conversion of the o-nitrobenzyl-C-glucoside to a sugar lactone
Kohri, M; Kimura, T; Shinoda, Y; Taniguchi, T; Nakahira, T
| HERO ID | 1039487 |
|---|---|
| In Press | No |
| Year | 2011 |
| Title | Photochemical conversion of the o-nitrobenzyl-C-glucoside to a sugar lactone |
| Authors | Kohri, M; Kimura, T; Shinoda, Y; Taniguchi, T; Nakahira, T |
| Journal | Carbohydrate Research |
| Volume | 346 |
| Issue | 18 |
| Page Numbers | 2965-2969 |
| Abstract | A new family of activated glycosidic compounds has been designed and synthesized: (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-nitrophenylmethane (1). It is stable in conditions commonly used for synthesis, and it can be converted to a sugar lactone derivative merely by photoirradiation (λ=365 nm): 2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone (2). A mechanism for the reaction is proposed. The photochemical conversion of 1 in the presence of methanol has also been demonstrated, giving rise to methyl 2,3,4,6-tetra-O-acetyl-D-gluconate (3). |
| Doi | 10.1016/j.carres.2011.10.027 |
| Pmid | 22070832 |
| Wosid | WOS:000299062800018 |
| Is Certified Translation | No |
| Dupe Override | No |
| Comments | Source: Web of Science 000299062800018 |
| Is Public | Yes |
| Language Text | English |
| Keyword | Photochemical conversion; o-Nitrobenzyl group; Sugar lactone |
| Is Qa | No |