title: A ring closing metathesis strategy for carbapyranosides of xylose and arabinose.
abstract: The synthesis of β-carba-xylo and arabino pyranosides of cholestanol is described. The synthetic strategy, which is analogous to the Postema approach to C-glycosides, centers on the ring closing metathesis of an enol ether-alkene precursor to give a cyclic enol ether that is elaborated to a carba-pyranoside via hydroboration-oxidation on the olefin. The method, which is attractive for its modularity and stereoselectivity, may find wider applications to carba-hexopyranosides and other complex cycloalkyl ether frameworks.
authors.affiliation: Department of Chemistry, Hunter College and The Graduate Center of the City University of New York, New York, NY 10016, USA.
authors.forename: Clayton E
authors.initials: CE
authors.lastname: Mattis
authors.affiliation: Department of Chemistry, Hunter College and The Graduate Center of the City University of New York, New York, NY 10016, USA. Electronic address: dmootoo@hunter.cuny.edu.
authors.forename: David R
authors.initials: DR
authors.lastname: Mootoo
mesh_terms: D001089:Arabinose / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D014994:Xylose / Q000737:chemistry*
chemical_list: D005960:Glucosides; D014994:Xylose; D001089:Arabinose
keywords: Arabinose; Carbasugar; Cholestanol (PubChem CID: 6665); Cycloalkyl ether; Dimethyl sulfide borane (PubChem CID: 9833925); Glycomimetic; Grubbs catalyst 2nd generation (PubChem CID: 11147261); Methyl (triphenylphosphoranylidene)acetate (PubChem CID: 17453); Methyl 2,3-O-isopropylidene-beta-d-ribofuranoside (PubChem CID: 96666); Methyl alpha-d-arabinofuranoside (PubChem CID: 11389582); RCM; Tebbe reagent (PubChem CID: 91617563); Xylose