发明名称 |
A method of preparing (3R,4R)-3-Hydroxy-4-Hydroxymethyl-4-butanolide. |
摘要 |
<p>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.</p> |
申请公布号 |
EP0581215(A2) |
申请公布日期 |
1994.02.02 |
申请号 |
EP19930111843 |
申请日期 |
1993.07.23 |
申请人 |
JAPAN TOBACCO INC. |
发明人 |
MATSUMOTO, KATSUYA;EBATA, TAKASHI;KOSEKI, KOSHI;OKANO, KOJI;KAWAKAMI, HIROSHI;MATSUSHITA, HAJIME |
分类号 |
C07D307/33;C07D493/04;C07D493/08;C07D493/18;C07H3/10;(IPC1-7):C07D307/32 |
主分类号 |
C07D307/33 |
代理机构 |
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代理人 |
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主权项 |
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地址 |
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