Unique reactions of glycosyl iodides with oxa- and thiocycloalkane acceptors.
[reaction: see text] Glucosyl-, galactosyl-, and mannosyl iodides efficiently react with strained oxacycloalkane acceptors to afford O-glycosides with high beta-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, beta-thiomannosides were synthesized from thiocycloalkane acceptors.
Dabideen
Darrin R
DR
Department of Chemistry, University of California Davis, Davis, California 95616, USA.
Gervay-Hague
Jacquelyn
J
D003516:Cycloparaffins / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry; D004988:Ethers, Cyclic / Q000737:chemistry; D006001:Glycoconjugates / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D014297:Trimethylsilyl Compounds
D003516:Cycloparaffins; D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D006001:Glycoconjugates; D006027:Glycosides; D014297:Trimethylsilyl Compounds; C419804:trimethylsilyl iodide; C013690:styrene oxide; C009068:propylene oxide