Synthesis of 5-epi-deoxynojirimycin from methyl alpha-D-glucoside
Witkowski, G; Kowalski, M; Szyszka, L; Potopnyk, MA; Jarosz, S
| HERO ID | 4854467 |
|---|---|
| In Press | No |
| Year | 2016 |
| Title | Synthesis of 5-epi-deoxynojirimycin from methyl alpha-D-glucoside |
| Authors | Witkowski, G; Kowalski, M; Szyszka, L; Potopnyk, MA; Jarosz, S |
| Journal | Tetrahedron: Asymmetry |
| Volume | 27 |
| Issue | 16 |
| Page Numbers | 747-752 |
| Abstract | A simple method for the preparation of 5-epi-nojirymycin (5-epi-DNJ) by a reductive amination of sugar derived alkoxyamines is presented. The latter were prepared in situ from the respective alkylated sugar oximes, which were obtained from the readily available methyl alpha-D-glucoside in a few well defined steps. The stereoselectivity of the reductive amination/cyclisation step depended on the size of the alkyl group in the oxime moiety and was best for the derivative decorated with a bulky tert-butoxyl group (5-epi-DNJ:DNJ = 82:18). The stereochemical outcome of this reaction was rather surprising since the analogous process performed for sugar alkylamines usually provides predominantly derivatives of DNJ. (C) 2016 Elsevier Ltd. All rights reserved. |
| Doi | 10.1016/j.tetasy.2016.06.011 |
| Wosid | WOS:000381170900005 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |