A ring closing metathesis strategy for carbapyranosides of xylose and arabinose.
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.
['Mattis|Clayton E|CE|', 'Mootoo|David R|DR|']
D000475:Alkenes D001089:Arabinose D060326:Chemistry Techniques, Synthetic D004083:Cholestanol D003500:Cyclization D004987:Ethers D006027:Glycosides D010084:Oxidation-Reduction D014994:Xylose
Xylose Arabinose Cycloalkyl ether Carbasugar Cholestanol (PubChem CID: 6665) 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)