Bis-desulfoglucosinolates:: A new class of bolaforms

Bis-desulfoglucosinolates 14-18 bearing D-gluco, lacto, malto and cellobio saccharidic moieties were synthesized in two steps from the corresponding protected 1-thio-beta-D-glycopyranoses 5, 8, 10 and 12 and bis-hydroximoyl chlorides 3a and 4a derived from 1,8-octanedial (1) and 1,12-dodecanedial (2). Fully deprotections of the intermediate O-acetylated derivatives 6, 7, 9, 11 and 13 were realized either using Zemplen method or methanol/triethylamine/water mixture, the choice of the conditions being dependent on the solubility in methanol of the fully and partially acetylated derivatives.