title: Alkylalanes and methyl furanosides: regioselective O-debenzylation or acetal cleavage.
abstract: Perbenzylated methyl pentofuranosides were submitted to the action of three alkylalanes and regioselective debenzylation at O-2 of the four pentoses was observed when choosing the right match between anomeric configuration and aluminium reagent. Diisobutylalane (DIBAL-H) allowed an easy access to reduced open-chain compounds, whereas trimethylalane (TMAL) stereoselectively produced methylated open chain derivatives.
authors.affiliation: Ecole Normale Supérieure, Département de Chimie, UMR 8642 CNRS, 24 rue Lhomond, F-75005 Paris, France.
authors.forename: Cai
authors.initials: C
authors.lastname: Jia
authors.forename: Yongmin
authors.initials: Y
authors.lastname: Zhang
authors.forename: Li-He
authors.initials: LH
authors.lastname: Zhang
authors.forename: Pierre
authors.initials: P
authors.lastname: Sinaÿ
authors.forename: Matthieu
authors.initials: M
authors.lastname: Sollogoub
mesh_terms: D000080:Acetals / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D009682:Magnetic Resonance Spectroscopy; D008759:Methylglycosides / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D001593:Benzyl Compounds; D008759:Methylglycosides