Streamlined Synthesis of Per-O-acetylated Sugars, Glycosyl Iodides, or Thioglycosides from Unprotected Reducing Sugars1

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

Research output: Contribution to journalArticlepeer-review

119 Citations (Scopus)

Abstract

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
Volume69
Issue number22
DOIs
Publication statusPublished - 2004

Cite this