Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 22, Pages 8719-8722Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo030073b
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Solvent-free per-O-acetylation of hexoses with a stoichiometric amount of acetic anhydride employing 0.03 mol % Cu(OTf)(2) proceeded in high yields (90-99%) at room temperature to give exclusively pyranosyl products as an anomeric mixture, the alpha/beta ratio of which was dependent on the temperature and amount of catalyst used. Sequential anomeric substitution with p-thiocresol in the presence of BF3.etherate gave the thioglycosides, isolated exclusively or predominantly as one anomer in 66-75% yields.
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