AN IMPROVED PREPARATION OF CYCLOHEXYLAMMONIUM ALLYL AND D-GLYCER-1'-YL 6-DEOXY-6-C-SULFONATO-ALPHA-D-GLUCOPYRANOSIDES

Potassium 6-deoxy-6-C-sulfonato-D-glucopyranose (sulfoquinovose) was r efluxed with allyl alcohol and Dowex-50 (H+) to give allyl 6-deoxy-6-C -sulfo-alpha-D-glucopyranoside (1), crystallised as the cyclohexylammo nium salt. Oxidation of this by permanganate gave DL-glycer-1'-yl 6-de oxy-6-C-sulfo-alpha-D-glucopyranoside, crystallised as the brucinium s alt. Conversion of the latter to the cyclohexylammonium salt allowed c rystallisation of glycer-1'-yl 6-deoxy-6-C-sulfonato-alpha-D-glucopyra noside (3-alpha-D-sulfoquinovosyl-sn-glycerol) (2) as almost entirely the D-glyceryl diastereoisomer. (C) 1998 Elsevier Science Ltd. All rig hts reserved.