Japan Tobacco Inc.

Yuji Gosei Kogyo Co., Ltd.

Katsuya Matsumoto

Hajime Matsushita

Takashi Ebata

Hiroshi Kawakami

Koshi Koseki

Koji Okano

Kazuo Itoh

Yoshitake Naoi

Hajime Yoshikoshi

Masakazu Okaniwa

Method of producing cis-whiskey lactone

Method of manufacturing D-allosan

Method of preparing epoxide

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 of manufacturing 3-DPA-lactone

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

Growing community of inventors

Yokohama, Japan

Katsuya Matsumoto