Dimethyl (-)-2,3-O-Isopropylidene-L-tartrate 37031-29 …

Analogous reagents have been prepared that employ different ketal protecting groups and which offer preparative and handling advantages over the isopropylidene ketal-derived reagent. Notable amongst them are (4)-2,2-diethyl-1,3-dioxolane-4-carboxaldehyde (3), and (2)-dioxaspiro[4,5]decane-2-carboxaldehyde (4). Both have found use in comparable synthetic situations since their introduction, though to a lesser extent than the reagent itself.

-Dimethyl 2,3-O-isopropylidene-L-tartrate

The reagent is readily elaborated into several other key chiral building blocks, most notably the corresponding protected glycerol, (4)-2,2-dimethyl-1,3-dioxolane-4-methanol (1), obtained by sodium borohydride reduction on aqueous solutions of the reagent. The 3-[()-2,2-dimethyl-1,3-dioxolan-4-yl]-2-propenoic acid esters 2, mentioned previously, have also found significant use in synthesis.

-Dimethyl-2,3-O-isopropylidene tartrate