Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
The Wittig olefinations of 2,3-O-isopropylidene-D-ribofuranose (1) with two equivalents of alkylidenetriphenylphosphorane (alkylidene: hexylidene - undecylidene) followed by hydrogenation catalyzed by palladium on carbon and subsequent deprotection yield (2R,3S,4S-(“L-”ribo)-1,2,3,4-alkanetetrols 5. These amphiphiles form the smectic A mesophase on melting. However, when 1 is heated with one equivalent of the alkylidenetriphenylphosphoranes for longer periods, (2R,3S,4R)-(“D-lyxo”)-1,2,3,4-alkanetetrol-type products 4 predominate.
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