An improved preparation of cyclohexylammonium allyl and d-glycer-1′-yl 6-deoxy-6-C-sulfonato-α-d-glucopyranosides

Potassium 6-deoxy-6-C-sulfonato-d-glucopyranose (sulfoquinovose) was refluxed with allyl alcohol and Dowex-50 (H+) to give allyl 6-deoxy-6-C-sulfo-α-d-glucopyranoside (1), crystallised as the cyclohexylammonium salt. Oxidation of this by permanganate gave dl-glycer-1′-yl 6-deoxy-6-C-sulfo-α-d-glucopyranoside, crystallised as the brucinium salt. Conversion of the latter to the cyclohexylammonium salt allowed crystallisation of glycer-1′-yl 6-deoxy-6-C-sulfonato-α-d-glucopyranoside (3-α-d-sulfoquinovosyl-sn-glycerol) (2) as almost entirely the d-glyceryl diastereoisomer.