Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1388913 | Carbohydrate Research | 2007 | 6 Pages |
3,4,6-Tri-O-acetyl-d-galactal, 3,4,6-tri-O-acetyl-d-glucal and 3,6,2′,3′,4′6′-hexa-O-acetyl-d-lactal were reacted with N-hydroxymethylphthalimide and boron trifluoride etherate to produce the corresponding phthalimidomethyl unsaturated glycosides via Ferrier rearrangement. When the galactal derivative was used, a non-Ferrier rearrangement product was also isolated as a minor product under classical Ferrier conditions. Phthalimidomethyl deoxy glycosides were readily prepared by hydrogenation of the unsaturated glycosides. Following deacetylation, the anti-inflammatory activities of these compounds were tested on mice and three were found to possess potent activity compared to hydrocortisone sodium succinate (HSS).
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