Unique reactions of glycosyl iodides with oxa- and thiocycloalkane acceptors

Darrin R. Dabideen, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticle

31 Citations (Scopus)

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

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styrene oxide
Iodides
iodides
glucosides
propylene oxide
Enantiomers
enantiomers
Glycosides
styrenes
selectivity
oxides
rings
Experiments

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Unique reactions of glycosyl iodides with oxa- and thiocycloalkane acceptors. / Dabideen, Darrin R.; Gervay-Hague, Jacquelyn.

In: Organic Letters, Vol. 6, No. 6, 18.03.2004, p. 973-975.

Research output: Contribution to journalArticle

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