The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
May. 02, 1995
Filed:
Jul. 23, 1993
Katsuya Matsumoto, Yokohama, JP;
Takashi Ebata, Yokohama, JP;
Koshi Koseki, Yokohama, JP;
Koji Okano, Yokohama, JP;
Hiroshi Kawakami, Yokohama, JP;
Hajime Matsushita, Yokohama, JP;
Japan Tobacco Incorporated, Tokyo, JP;
Abstract
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.