SYNTHETIC INTERMEDIATE FOR CONAGENIN AND ITS PRODUCTION

摘要

PURPOSE: To obtain a new compound useful for converting conagenin which is a low-molecular immunomodulator and its derivative as a synthetic reagent, an organic synthetic reagent or an organic new material. CONSTITUTION: The optically active alcohol derivative of formula I (R<1> to R<4> are each H, a <=3C alkyl, etc.; R<5> is H, benzyl, t-butylsilyl, an aryl or o- nitrobenzyl). The compound of formula I is obtained by protecting the OH group of an alcohol derivative of formula II with acetonide, providing an optically active diol derivative, then catalytically reducing the resultant diol derivative and removing the protecting group. Furthermore, a new optically activeα,α-disubstituted oxazinone derivative of formula III (R<8> and R<9> are each a <=4C alkyl, phenyl, etc.; R<10> is tertiary butoxycarbonyl, benzyl, etc.; R<11> is a <=3C alkyl; R<12> is H, methoxymethyl, etc.) and its intermediate are within the scope of this invention. The compound is useful as a low-molecular immunomodulator, a synthetic intermediate, etc., for anα-methylserine segment of conagenin.