Unique reactions of glycosyl iodides with oxa- and thiocycloalkane acceptors

Darrin R. Dabideen, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

Abstract

(Equation presented) Glucosyl-, galactosyl-, and mannosyl iodides efficiently react with strained oxacycloalkane acceptors to afford O-glycosides with high β-selectivity. The mechanism of ring opening was investigated by reacting mannosyl iodides with pure enantiomers of propylene oxide and styrene oxide. Competition experiments between three- and five-membered oxacycloalkanes were also investigated. Finally, β-thiomannosides were synthesized from thiocycloalkane acceptors.

Original languageEnglish (US)
Pages (from-to)973-975
Number of pages3
JournalOrganic Letters
Volume6
Issue number6
DOIs
StatePublished - Mar 18 2004

ASJC Scopus subject areas

  • Molecular Medicine

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