Unique Reactions of Glycosyl Iodides with Oxa- and Thiocycloalkane Acceptors

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 ex...

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Bibliographic Details
Published in:Organic letters 2004-03, Vol.6 (6), p.973-975
Main Authors: Dabideen, Darrin R, Gervay-Hague, Jacquelyn
Format: Article
Language:English
Subjects:
Cycloparaffins - chemistry
Epoxy Compounds - chemistry
Ethers, Cyclic - chemistry
Glycoconjugates - chemistry
Glycosides - chemical synthesis
Glycosides - chemistry
Glycosylation
Molecular Structure
Trimethylsilyl Compounds
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol049966w