Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1995-12-18
1997-08-05
Richter, Johann
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
554143, 560263, 5625124, 562590, 562595, C07C 5136, C07C 6966, C07C 3120
Patent
active
056544723
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP95/00749 filed Apr. 17, 1995.
TECHNICAL FIELD
The present invention relates to a novel glycerol derivative and a process for preparing the same, and a process for preparing a triazole derivative. More particularly, the invention relates to a novel glycerol derivative, being useful as a raw material for synthesizing a medicament, an agricultural chemical or the like and a process for preparing the same and a process for preparing a triazole derivative.
BACKGROUND ART
Hitherto, a compound useful as a raw material of a medicament or biologically active substance has been variously studied. However, there was no suitable compound from various viewpoint of economy and industry, according to demands for a glycerol derivative and an acetone derivative which can be used as a raw material for synthesizing a medicament, an agricultural chemical or the like. For instance, 1-chloro-2-(2,4-difluorophenyl)-2,3-epoxypropane is synthesized by carrying out ring closure of epoxide using 1,3-dichloro-2-(2,4-difluorophenyl)-2-propanol in the presence of sodium hydride in dimethylformamide, in Japanese Unexamined Patent Publication No. 9183/1993. However, this reaction had problems in industrially carrying out the reaction such as evolution of hydrogen and difficult removal of dimethylformamide after completion of the reaction.
Thus, the compounds which satisfy the various demands such as an 2-aryl-1,3-diacyloxy-2-propanol and a 1,3-diacyloxyacetone being the compounds of the present invention have not been synthesized until now, and there is no existing knowledge as to the preparation thereof. Also, there is no report that the optically active 2-aryl-3-acyloxy-1,2-propanediol represented by the formula (VIII): ##STR1## has been synthesized or isolated. The above-mentioned compounds of the formula (VIII) including a 2-(2,4-difluorophenyl)-2-acyloxy-1,2-propanediol wherein an aryl group is 2,4-difluorophenyl group are novel compounds, and the industrial process for preparing the same have not been established at present. Further, there is not disclosure as to an optically active compound represented by the formula (IX): ##STR2## and a process for preparing the same, and thus these compounds are novel compounds. Then, a result of the continuous effort of the present inventors as to a glycerol derivative and an acetone derivative which can be used as a raw material for synthesizing a medicament, a biologically active substance or the like and a process for preparing the same; a novel glycerol derivative, a novel acetone derivative and novel processes for preparing the same have been established. According to the present invention, there can be also easily prepared the optically active 2-aryl-2,3-epoxy-1-propanol being an intermediate for synthesizing a medicament, which was hitherto synthesized by subjecting to cyclization, in the presence of a base, and hydrolysis from an 2-aryl-2-propenol by the of complecated Sharpless epoxidation reaction (ref. the specification of European Patent No. 0539938) and the like. Also, a novel process for preparing a triazole derivative being a compound useful as an intermediate of an antifungal agent (ref. Japanese Unexamined Patent Publication No. 9183/1993 and the specification of European Patent No. 539938). Furthermore, an 2-aryl-1,2,3-propanetriol represented by the formula (III): ##STR3## is a novel compound, and a process for synthesizing the same is also novel. The present inventors also estabilished processes for preparing those compounds.
The object of the present invention is to provide a novel 1,3-diacyloxyacetone, an optically active 2-arylglycerol derivative which are useful are as a raw material of a medicament or a biologically active substance and processes for preparing them, and a novel process for preparing an intermediate for an existing medicament.
DISCLOSURE OF THE INVENTION
The present invention relates to an 2-aryl-1,3-diacyloxy-2-propanol compound represented by the formula (I): ##STR4## wherein Ar is an aryl group which may be
REFERENCES:
"Thymol Derivatives From Schizogyne Glaberrima"--Gonzalez et al, Phytochemistry, vol. 25, No. 12, pp. 2889-2891 (1986).
"New Guaianolides From Centipedaminima", Bohlmann et al., Kexue Tongbao, vol. 29, No. 7, pp. 900-903 (Jul. 1984).
Hasegawa Junzo
Kawano Shigeru
Kizaki Noriyuki
Miyamoto Kenji
Yasohara Yoshihiko
Kanegafuchi Kagaku Kogyo & Kabushiki Kaisha
Oswecki Jane C.
Richter Johann
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