RESUMEN
In this note, supercritical fluid chromatography coupled to high-resolution mass spectrometry (SFC-HRMS) has been used to identify a chloro glycoside formed during the preparation of propargyl 1,2-orthoesters in dichloromethane. Additional studies revealed that 20-40% of this side-product was obtained depending on the source of anhydrous solvent, and that tetrabutylammonium iodide amplifies this side-reaction. Finally, a reliable procedure was developed in acetonitrile to prepare these glycosyl donors from perbenzoylated bromo glycosides in manno, gluco and galacto series in 63-74% yield.
Asunto(s)
Glicósidos , Cloruro de Metileno , Acetonitrilos , Glicósidos/química , Hexosas , Espectrometría de Masas , SolventesRESUMEN
An unprecedented hydroalumination of C â O bonds catalyzed by zirconocene dichloride is reported herein and applied to the site-selective deprotection of peracetylated functional substrates. A mixed metal hydride, with 1:1 zirconium/aluminum stoichiometry, is also shown to be the reductive species. A catalytic cycle is finally proposed for this transformation with no precedent in the field of zirconium catalysis.