Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 69, Issue 22, Pages 7758-7760Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo048890e
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- Biotechnology and Biological Sciences Research Council [BBS/E/J/000C0618] Funding Source: Medline
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Solvent-free per-O-acetylation of sugars with stoichiometric acetic anhydride and catalytic iodine proceeds in high yield (90-99%) to give exclusively pyranose products as anomeric mixtures. Without workup, subsequent anomeric substitution employing iodine in the presence of hexamethyldisilane (i.e., TMS-I generated in situ) gives the corresponding glycosyl iodides in 75-95% isolated yield. Alternatively, and without workup, further treatment with dimethyl disulfide or thiol (ethanethiol or thiocresol) gives anomerically pure thioglycosides in more than 75% overall yield.
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