29 research outputs found

    Mild and Highly Efficient Stereoselective Synthesis of 2,3-Unsaturated Glycopyranosides using La(NO3)3 · 6H2O as a Catalyst: Ferrier Rearrangement

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    A mild and highly efficient stereoselective reaction of 3,4,6-tri-O-acetyl-D-glucal with a variety of nucleophiles, viz. alcohols, phenols, thiols, thiophenols, and allyl trimethyl silane (TMS), in the presence of 5 mol% of lanthanum(III) nitrate hexahydrate under solvent-free conditions yielded the corresponding 2,3-unsaturated glycopyranosides (pseudoglycals) in excellent yields
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