Journal
SYNTHETIC COMMUNICATIONS
Volume 38, Issue 2, Pages 170-176Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/00397910701744170
Keywords
alcohols; allyl TMS; La(NO3)(3) center dot 6H(2)O; phenols; thiols; 3,4,6-tri-O-acetyl-D-glucal
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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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