Topic
Ferrier rearrangement
About: Ferrier rearrangement is a research topic. Over the lifetime, 321 publications have been published within this topic receiving 5524 citations.
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TL;DR: In this paper, a simple, mild, efficient and environmentally benign method for the synthesis of 2,3-unsaturated allyl C-glycosides and O- and S-Glycosides is described using phosphomolybdic acid supported on silica gel as a reusable catalyst with high α-selectivity.
Abstract: A simple, mild, efficient and environmentally benign method for the synthesis of 2,3-unsaturated allyl C-glycosides and O- and S-glycosides is described using phosphomolybdic acid supported on silica gel as a reusable catalyst with high α-selectivity.
1 citations
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TL;DR: In this paper, the Ferrier rearrangement of a methyl α-d -mannopyranoside derivative (8a), followed by a stereoselective reduction gave a l -chiro-inositol derivative (2), which was converted to l -myo- inositol 1,2,3-trisphosphate (3) and l -chirosin-inotransformer 1, 2,3,5-tetrakisphophosphate(4).
Abstract: The Ferrier rearrangement of a methyl α- d -mannopyranoside derivative (8a), followed by a stereoselective reduction gave a l -chiro- inositol derivative (2), which was converted to l -chiro- inositol 1,2,3-trisphosphate (3) and l -chiro- inositol 1,2,3,5-tetrakisphosphate (4). Compounds 3 and 4 may be considered to be the C3-position stereoisomers of d -myo- inositol 1,2,6-trisphosphate (α-trinositol) and d -myo- inositol 1,3,4,5-tetrakisphosphate, respectively, and should be useful for the binding studies with their macromolecular counterparts.
1 citations
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TL;DR: Eletrolysis with a Zr anode generates a soluble zirconium species which promotes the Ferrier rearrangement of peracylated glucal in the presence of nucleophiles.
Abstract: Eletrolysis with a Zr anode generates a soluble zirconium species which promotes the Ferrier rearrangement of peracylated glucal (I) in the presence of nucleophiles and the hetero Michael addition of nucleophiles to enone (VII)
1 citations
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TL;DR: Tm(OTf)3 is shown to be a highly efficient catalyst for the preparation of various 2,3-unsaturated glycosides in Ferrier rearrangement reactions as mentioned in this paper.
Abstract: Tm(OTf)3 is shown to be a highly efficient catalyst for the preparation of various 2,3-unsaturated glycosides in Ferrier rearrangement reactions.
1 citations
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TL;DR: In this paper, the preparation of eight 2,3-unsaturated O-glycosides from D-glycals and alcohols, using montmorillonite K-10 as an acid catalyst, is described.
Abstract: Abstract The preparation of eight 2,3-unsaturated O-glycosides from D-glycals and alcohols, using montmorillonite K-10 as an acid catalyst, is described. The Ferrier rearrangement products were obtained in good yields using conventional heating and microwave irradiation but the reaction time was substantially reduced employing the latter procedure. The yields were slightly lower under microwave exposure. Five of the di-O-acetylated products were deacetylated to the glycosides in excellent yields. The acetylated products possess good anti-inflammatory property suggesting that the acetyl group plays an important role in reducing the inflammation. Among the compounds tested, glycosides containing thiophene as an aglycone present much better inflammation reducing characteristics than the analogues without this function.
1 citations