A Short and Convenient Synthesis of 1-Deoxymannojirimycin and N-Oxy Analogues from D-Fructose.

Ketonitrone I was prepd. from D-fructose as an inexpensive starting material and was used in a stereoselective synthesis of 1-deoxymannojirimycin (DMJ), of its previously unknown N-hydroxy analog II, and of the polyhydroxylated ketonitrone III. The latter were assayed as potential glycosidase inhibitors on a panel of 13 selected purified enzymes. Disappointingly, the polyhydroxylated nitrone III inhibited none of these enzymes. However, II exhibited a moderate and non-selective activity toward the snail $\beta$-mannosidase EC 3.2.1.25. [on SciFinder(R)]

Références

Titre
A Short and Convenient Synthesis of 1-Deoxymannojirimycin and N-Oxy Analogues from D-Fructose.
Type de publication
Article de revue
Année de publication
2009
Revue
J. Org. Chem.
Volume
74
Pagination
1766–1769
ISSN
0022-3263
Soumis le 12 avril 2018