Studies in Stereochemistry. XIII. dl-Phenylserinols : A New Synthesis and its Stereochemical Findings. (5)

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概要

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• In the new route to N-benzoyl-dl-threo-phenylserinol which has been reported in the previous papers, the formation of dl-erythro-1-phenyl-1,2-dibromoprop-3-yl benzimino ether is intermediately involved. In the present series acetonitrile was used instead of benzonitrile in the analogous process and the whole process was placed under consideration. It was found that in the acidic solvolysis of dl-threo-1-phenyl-1-bromo-2-amino-3-acetoxypropane hydrochloride, the displacement of C_1-Br by OH-was effected with overall retention, particularly accompanying with the fission of O-acetyl group. In contrast with the same treatment of the O-benzoyl analog which as has been reported, resulted in inversion and retention without fission of the O-benzoyl group, the effect of the O-acetyl fission upon stereochemical results was examined and the mechanism was discussed.

• 公益社団法人日本薬学会の論文

著者

• 古賀 俊隆

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 友枝 宗光

  Eisai Co., Ltd.

• 友枝 宗光

  Eisai Co. Ltd.

• 古賀 俊隆

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 田口 胤三

  Pharmaceutical Institute, Medical Faculty, University of Kyushu

• 友枝 宗光

  Pharmaceutical Institute, Medical Faculty, University of Kyushu

• 古賀 俊隆

  Pharmaceutical Institute, Medical Faculty, University of Kyushu

• 田口 胤三

  Pharmaceutical Institute Medical Faculty University Of Kyushu

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