Streamlined synthesis of per-O-acetylated sugars, glycosyl iodides, or thioglycosides from unprotected reducing sugars

Balaram Mukhopadhyay, K. P. Ravindranathan Kartha, David A. Russell, Robert A. Field

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137 Citations (Scopus)


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.
Original languageEnglish
Pages (from-to)7758-7760
Number of pages3
JournalJournal of Organic Chemistry
Issue number22
Publication statusPublished - 25 Sep 2004

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