Synthesis of a 'reverse ester' analogue of 1,2-sn-diglycerides from (S)-1,2-di-O-isoprophylideneglycerol; efficient, stereospecific nucleophilic displacement via a triflate at glycerol C-2

Article abstract of DOI:10.1016/0040-4039(93)85070-D

An optically pure glyceride analogue in which the 2-O-ester grouping has been reversed was efficiently synthesised from (S)-di-O-isopropylideneglycerol by a sequence that featured an S_N 2 displacement by the anion of diethyl malonate on a protected glycerol 2-O-triflate.