PURPOSE: To obtain the subject compound, useful for a raw material, etc., for liquid crystals, medicines, agrochemicals, etc., by optically resolving a recemic 1-benzyloxy-6,6,6-trifluoro-4-hexyn-3-ol, then carrying out the reduction of the (S)-isomer into an olefin and conversion into a diol, etc.
CONSTITUTION: This method for producing a derivative of 6-deoxy-6,6,6- trifluorosaccharides represented by formula V (R1 and R2 are each an alkyl or an aryl) comprises optically resolving a recemic 1-benzyloxy-6,6,6-trifluoro-4- hexyn-3-ol represented by formula I, then reducing the resultant (S)-isomer in the presence of sodium hydride-bis(methoxyethoxy) aluminum, stereospecifically reduce the triple bond, providing (S, E)-1-benzyloxy-6,6,6- trifluoro-4-hexen-3-ol represented by formula II, subsequently oxidizing the resultant compound in the presence of osmimium tetroxide, afford a triol derivative represented by formula III, then converting the resultant triol derivative into an acetonide, debenzylating the prepared compound represented by formula IV and subsequently oxidizing the debenzylated compound. The resultant derivative is useful for liquid crystal materials, an intermediate for medicines, agrochemicals, etc.
YAMAZAKI TAKASHI
WATABE AKIO
