Glucosinolate Chemistry: Synthesis of O‐Glycosylated Derivatives of Glucosinalbin

Abstract

AbstractThe synthesis of the major glucosinolate of Moringa oleifera and of other non‐natural O‐glycosylated derivatives of glucosinalbin is reported. The synthetic sequence applied, which involves the conversion of carbohydrate‐based nitrostyrenes into the key thiohydroximates, appears to be sufficiently versatile to synthesize a range of glucosinolatesbearing a glycosylated phenolic function. We synthesizedanalogues of the naturally occurring L‐rhamnoside 1 with a view to estimating the importance of this phenol‐protecting sugar moiety in modulating the biological activity of the parent glucosinolate and related breakdown products.