Japan Tobacco Inc.

Yuki Gosei Kogyo Co., Ltd.

Fuji Flavor Co., Ltd.

Japan Tabacco Inc.

Japan Tobacco Co.

Yuji Gosei Kogyo Co., Ltd.

Topy Industries, Ltd. and Japan Tobacco, Inc.

Hajime Matsushita

Takashi Ebata

Koshi Koseki

Hiroshi Kawakami

Kyoko Takahashi

Makoto Shibagaki

Katsuya Matsumoto

Kazuo Itoh

Yoshitake Naoi

Hideyuki Kuno

Hiroshi Ichinose

Mikio Ono

Koji Okano

Shigeo Ishiguro

Akira Izumi

Junko Tanaka

Masataka Mori

Junji Ohki

Shigenobu Mizusaki

Sigenobu Mizusaki

Nobuhiro Mizutani

Hajima Yoshikoshi

Hajime Yoshikoshi

Ichiro Honda

Masakazu Okaniwa

Ikuo Horii

Masaru Yamamoto

Kenichiro Sugimori

Hiromi Kaibara

The present invention relates to a method of preparing an alcohol by reducing a carboxylic acid or a derivative thereof, more particularly, a method of preparing an alcohol by a reduction reaction in the presence of a zirconium-titanium oxide catalyst. A carboxylic acid or a carboxylic acid derivative is converted into a corresponding alcohol by a reduction reaction in the presence of a zirconium-titanium oxide catalyst using an alcohol as a hydrogen source. An alcohol can be prepared in a high yield in the present invention. To be more specific, the method of the present invention can convert a higher fatty acid or a carboxylic acid derivative, which has given a corresponding alcohol in a low yield in the presence of a zirconium catalyst alone, into the corresponding alcohol in a high yield. Further, the reaction can be performed easily, and the product can be easily separated from the catalyst.

Method of preparing an alcohol

Method of producing cis-whiskey lactone

Method of manufacturing D-allosan

Method of preparing epoxide

Disclosed is a method of obtaining (S)-(-)-3-(1-methyl-2-pyrrolidinyl)-2-pyridone (2) and (R)-(+)-3-(1-methyl-2-pyrrolidinyl)-2-pyridone (3) by resolving a racemic mixture of the compounds (2) and (3). More specifically, disclosed is a method of obtaining the optically active nicotine derivatives (2) and (3) shown below, which comprises steps of binding (.+-.)-3-(1-methyl-2-pyrrolidinyl)-2-pyridone to a sugar derivative, resolving the obtained compound into two types of stereoisomers, and treating them under an acidic condition. ##STR1##

Optical resolution method of a nicotine derivate

Method for preparing 2'-3'-dideoxy-.beta.-nucleosides using

Providing a method of preparing (3R,4R)-3-hydroxy-4-hydroxymethyl-4-butanolide conveniently and selectively from a widely available raw material in a high yield. A carbonyl group of the 2-position of levoglucosenone is reduced to obtain a hydroxyl group of a .beta.-configuration. Then, an iodo-group of an .alpha.-configuration and an acyloxy ion of a .beta.-configuration are introduced regioselectively and stereoselectively to the double bond at the 4-position and the 3-position of the above-mentioned levoglucosenone, respectively, keeping a trans stereochemical relationship. An alkoxide is then formed, by hydrolysis and an oxirane ring of a .beta.-configuration is formed by removing an iodo-group by intramolecular nucleophilic displacement reaction of the alkoxide. After the hydroxyl group of the 2-position is oxidized to convert to a carbonyl group, the oxirane ring is reductively and selectively cleaved, thereby obtaining a chemical compound having no substituent at the 3-position and a hydroxyl group of a .beta.-configuration at the 4-position. Finally a lactone of 5-membered-ring is prepared by subjecting the above-obtained compound to Baeyer-Villigar oxidation.

Method of preparing (3R,4R)-3-hydroxy-4-hydroxymethyl-4-butanolide

method of preparing D-altrose

Method of preparing 3-DPA-lactone

Method for manufacturing 4-substituted-Y-lactone and novel substance

Method of manufacturing 3-DPA-lactone

A method for producing (R,Z)-5-tetradecen-4-olide, comprising the following reaction formulas; ##STR1##

Method for producing (R,Z)-5-tetradecen-4-olide

An acid addition salt of .delta.-aminolevulinic acid is prepared in such a way that tetrahydrofurfurylamine (VI) is reacted with phthalic anhydride under an anhydrous condition to introduce a phthal group which protects amino group of tetrahydrofurfurylamine to give N-tetrahydrofurfuryl phthalimide (III), carbon atoms of the first- and fourth-positions of thus obtained N-tetrahydrofurfurylphthalimide (III) are oxidized at 80.degree. C. using sodium periodate as a oxidizing agent and ruthenium chloride hydrate as a catalyst to yield 5-phthalimidolevulinic acid (II), then the protecting group of 5-phthalimidolevulinic acid (II) is deprotected using an acid to prepare an acid additional salt of .delta.-aminolevulinic acid. The acid additional salt of .delta.-aminolevulinic acid is readily converted by neutralization by an alkali to .delta.-aminolevulinic acid, which is very useful as a precursor of Vitamin B.sub.12, heme and chlorophyll.

Method of preparing an acid additional salt of delta-aminolevulinic acid

The instant invention is drawn to a method for manufacturing 2',3'-dideoxy-2',3'-didehydronucleoside compounds by reacting a ribonucleoside derivative wherein the hydroxyl in the 5'-position of the furanose ring of said ribonucleoside is protected by a silyl protective group, with an acid anhydride such as acetic anhydride in the presence of a catalyst such as hydrous zirconium oxide, and then subjecting the reaction product to decarboxylation. The decarboxylation can be effected by heating the reaction product. This method can be performed in a single step, and requires no reagents which are expensive or chemicals which should be handled with care. Hence, it serves to manufacture 2',3'-dideoxy-2',3'-didehydronucleosides easily at low cost.

Method of manufacturing 2',3'-dideoxy-2',3'-didehydronucleosides

2'-deoxy-.beta.-adenosine can be industrially and easily obtained without using expensive or dangerous materials by the process of the present invention, which comprises the steps of: preparing a salt of adenine from adenine, allowing to condense the salt with a derivative of pentofuranose to isolate a derivative of adenine, and then eliminating the protecting groups.

Process for preparing 2'-deoxy-.beta.-adenosine

Growing community of inventors

Yokohama, Japan

Hajime Matsushita