Reactions of per-O-benzoyl-β-D-galf isothiocyanate, a chiral resolving agent

Article abstract of DOI:10.1016/S0040-4020(97)10070-9

Tetra-O-benzoyl-β-D-galactofuranosyl isothiocyanate (1) was readily prepared (90% yield) from per-O-benzoyl-D-galactofuranose, via the glycosyl bromide. Reaction of 1 with alcohols, amines and amino acids afforded a variety of glycosylthiourethanes and glycosylthioureides. The isothiocyanate 1 showed to be useful as a chiral resolving agent. The resolution of recemic primary and secondary mines and aminoalcohols was readily accomplished, in analytical and preparative scale, by condensation of such compounds with 1.