PURPOSE: To obtain the titled stereospecific compound, by reacting a novel compound as a raw material with a specific compound, reducing the resultant novel intermediate, sulfonating the reduction product, reacting the sulfonated compound with a sulfide, and finally eliminating the cyclohexyl group.
CONSTITUTION: A highly crystalline novel 3,4-O-cyclohexylidene-D-arabinose as a raw material is reacted with a [3-alkoxycarbonyl-propen -(2)-ylidene-(1)]triphenylphosphorane and the resultant intermediate is then re duced and sulfonated. The resultant sulfonated compound is further reacted with a sulfide and the cyclohexyl group is finally eliminated under acidic conditions to afford the aimed (2S, 3R, 4S)-2-[4-(alkoxycarbonyl)butyl]-3,4- dihydrotetrahydrothiophene, expressed by the formula (R is lower alkyl) and useful as a synthetic intermediate for biotin in good yield.
HORISAKI TOSHIO
SHIMAKAWA YASUO
TAKAHASHI MINOICHI
MASUDA SATORU
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