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Synthesis of d ribo and l lyxo phytosphingosine transformation into the corresponding lactosylceramides


, : Synthesis of d ribo and l lyxo phytosphingosine transformation into the corresponding lactosylceramides. Carbohydrate Research 174: 169-180

2,4-O-Benzylidene-D-threose (2) reacted with tetradecylmagnesium bromide to give the D-arabino- and the L-xylo-octadecanetetrol derivatives 3a and 3x as a readily separable mixture. Each of these compounds was transformed, via regioselective mesylation, azide displacement, benzylidene cleavage, and azide reduction, into D-ribo- (1r) and L-lyxo-phytosphingosine (1l), respectively. 3,4-O-Isopropylidenation of the intermediate azido derivatives 7r and 7l afforded the 1-O-glycosyl acceptors 2-azido-3,4-O-isopropylidene-D-ribo-1,3,4-octadecanetriol (8r) and 2-azido-3,4-O-isopropylidene-L-lyxo-1,3,4-octadecanetriol (81), respectively. With the trichloroacetimidate-activated lactosyl donor 9, the expected glycosides 2-azido-1-O-(2,3,6,2',3',4',6'-hepta-O-acetyl-.beta.-lactosyl)-3,4-O-isopropylidene-D-ribo- and -L-lyxo-1,3,4-octadecanetriol (10r and 10l) were obtained, which were conveniently transformed into the corresponding unprotected glycosphingolipids 14r and 14l.

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