SnCl4: An efficient and inexpensive promoter for synthesis of ω-functionalized alkyl 1,2-trans-glycosides from 1-O-pivaloyl donor

Abstract

SnCl₄-promoted reactions of perpivaloylated lactose with various alcohols were studied in the presence or absence of an additive, CaCO₃. SnCl₄ was found to promote the 1,2-trans-glycosylation of alcohols in CH₂Cl₂ at 0°C in a stereo controlled manner with β-selectivity. The corresponding glycosides were isolated in high yields.