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    A method of preparing (3R,4R)-3-Hydroxy-4-Hydroxymethyl-4-butanolide
    1.
    发明公开
    A method of preparing (3R,4R)-3-Hydroxy-4-Hydroxymethyl-4-butanolide 失效
    （3R，4R）-3-羟基-4-羟甲基-4-丁醇酯。

    公开(公告)号：EP0581215A2

    公开(公告)日：1994-02-02

    申请号：EP93111843.4

    申请日：1993-07-23

    申请人： JAPAN TOBACCO INC.

    发明人： Matsumoto, Katsuya, c/o Japan Tobacco Inc. ,  Ebata, Takashi, c/o Japan Tobacco Inc. ,  Koseki, Koshi, c/o Japan Tobacco Inc. ,  Okano, Koji, c/o Japan Tobacco Inc. ,  Kawakami, Hiroshi, c/o Japan Tobacco Inc. ,  Matsushita, Hajime, c/o Japan Tobacco Inc.

    IPC分类号： C07D307/32

    CPC分类号： C07D307/33 ,  C07D493/08 ,  C07H3/10

    摘要： 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 β-configuration. Then, an iodo-group of an α-configuration and an acyloxy ion of a β-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 β-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 β-configuration at the 4-position. Finally a lactone of 5-membered-ring is prepared by subjecting the above-obtained compound to Baeyer-Villigar oxidation.

    摘要翻译： 提供从广泛获得的原料中以高收率方便和选择地制备（3R，4R）-3-羟基-4-羟甲基-4-丁醇的方法。 降低左旋葡萄糖酮的2-位的羰基，得到β-构型的羟基。 然后，分别对上述左旋葡萄糖酮的4-位和3-位分别选择性且立体选择性地引入α-构型的碘基和β-构型的酰氧基，保持 反式立体化学关系。 然后通过水解形成醇盐，通过醇盐的分子内亲核置换反应除去碘基形成β-构型的环氧乙烷环。 在2-位的羟基被氧化转化为羰基后，环氧乙烷环被还原和选择性地裂解，从而得到在3-位没有取代基的化合物和β构型的羟基在 4位。 最后通过将上述得到的化合物进行Baeyer-Villigar氧化来制备5元环的内酯。

    A method of preparing (3R,4R)-3-Hydroxy-4-Hydroxymethyl-4-butanolide
    3.
    发明公开
    A method of preparing (3R,4R)-3-Hydroxy-4-Hydroxymethyl-4-butanolide 失效
    制备（3R，4R）-3-羟基-4-羟甲基-4-丁内酯的方法

    公开(公告)号：EP0581215A3

    公开(公告)日：1994-04-13

    申请号：EP93111843.4

    申请日：1993-07-23

    申请人： JAPAN TOBACCO INC.

    发明人： Matsumoto, Katsuya, c/o Japan Tobacco Inc. ,  Ebata, Takashi, c/o Japan Tobacco Inc. ,  Koseki, Koshi, c/o Japan Tobacco Inc. ,  Okano, Koji, c/o Japan Tobacco Inc. ,  Kawakami, Hiroshi, c/o Japan Tobacco Inc. ,  Matsushita, Hajime, c/o Japan Tobacco Inc.

    IPC分类号： C07D307/32

    CPC分类号： C07D307/33 ,  C07D493/08 ,  C07H3/10

    摘要： 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 β-configuration. Then, an iodo-group of an α-configuration and an acyloxy ion of a β-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 β-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 β-configuration at the 4-position. Finally a lactone of 5-membered-ring is prepared by subjecting the above-obtained compound to Baeyer-Villigar oxidation.

    摘要翻译： 提供一种以高产率方便且选择性地从广泛可得的原料制备（3R，4R）-3-羟基-4-羟甲基-4-丁内酯的方法。 左旋葡聚糖酮的2-位的羰基被还原以获得β-构型的羟基。 然后，分别将α-构型的碘基和β-构型的酰氧基离子区域选择性立体选择性引入上述左旋葡聚糖酮的4-位和3-位的双键， 反式立体化学关系。 然后通过水解形成醇盐，并且通过醇盐的分子内亲核取代反应除去碘基而形成β-构型的环氧乙烷环。 在2位的羟基被氧化而转化为羰基后，环氧乙烷环被还原性选择性地切断，得到3位不具有取代基的化合物，以及β位不具有取代基的羟基 4位。 最后，通过将上述化合物进行Baeyer-Villigar氧化来制备5元环内酯。