Alkylalanes and methyl furanosides: regioselective O-debenzylation or acetal cleavage.
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.
Jia
Cai
C
Ecole Normale Supérieure, Département de Chimie, UMR 8642 CNRS, 24 rue Lhomond, F-75005 Paris, France.
Zhang
Yongmin
Y
Zhang
Li-He
LH
Sinaÿ
Pierre
P
Sollogoub
Matthieu
M
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
D000080:Acetals; D001593:Benzyl Compounds; D008759:Methylglycosides