CAS: 5405-40-3; (S)-3-Hydroxy-4,4-Dimethyldihydrofuran-2(3H)-One

该化合物是一个循环酯,具体地说是一个内酯,产自全硫酸,其特征是其手性,作为单一的对应体存在,有助于其生物活动,该化合物一般没有色状,可粉黄,有香味,在水和有机溶剂中可溶解. (+)-潘坦古酮因其在各种生化过程中的作用而闻名,特别是在碳水化合物和脂肪的代谢中,还因其温和甜味,在合成药物和食品工业中用作调味剂.该化合物在正常条件下具有稳定性,但在有强酸或碱的情况下可进行水解.其安全性特征表明毒性低,适合各种应用.

结构式图片

相似化合物

599-04-2 79-50-5 13031-04-4

欧盟法规

REACH注册ECHA物质C&L通报

上下游产品

Dl-泛酰内酯 Pantolactone 79-50-5
D-(-)-泛酰内酯 (R)-Pantolacton 599-04-2
(Rs)-2-Acetoxy-3,3-Dimethyl-γ-Butyrolactone 28227-35-2
(S)-2-Acetoxy-3,3-Dimethyl-γ-Butyrolactone 28387-34-0
γ-二甲基丁内酯 Pantoyllacton 13861-97-7
(R)-Ethyl 2-Hydroxy-3,3-Dimethyl-4-Oxobutanoate 1196498-52-8
(2S)-2,4-二羟基-3,3-二甲基丁酸 L-Pantoic Acid 1112-32-9
(S)-2-Hydroxy-3,3-Dimethyl-Bernsteinsaeuredimethylester 68984-72-5
(S)-3-(Benzyloxy)-4,4-Dimethyldihydrofuran-2(3H)-One

合成工艺路线路线简述

    2,2-二甲基-3-羟基丙醛置于水,Calcium Chloride,奎宁体系中,化学反应生成 (S)-(+)-泛解酸内酯
    参考文献:Reichstein; Gruessner,Helvetica Chimica Acta,1940,Vol. 23,P. 653
    标题:Reichstein; Gruessner,Helvetica Chimica Acta,1940,Vol. 23,P. 653

    海关参考信息

    专利信息


    专利号:WO-2023078722-A1
    优先权日:2021-11-02
    标题 :Synthesis of pantothenic acid butyrate
    发明人:BONRATH WERNER; EGGERTSWYLER CHRISTOPHE; PACE FRANCESCO
    权利人:DSM IP ASSETS BV
    摘要:The present invention relates to new specific butyrate compounds to a new and improved synthesis of specific butyrates as well their use. Butyrate compounds are very useful compounds, either as such or as intermediates in organic synthesis.

    专利号:WO-2019228873-A1
    优先权日:2018-05-31
    标 题:Synthesis of a racemic mixture of pantolactone
    发明人:BONRATH WERNER; BOURGEOIS FREDERIC; MEDLOCK JONATHAN; SPARR CHRISTOF
    权利人:DSM IP ASSETS BV
    摘要:The invention relates to an improved synthesis of a racemic mixture of pantolactone (I).

    专利号:WO-2019228874-A1
    优先权日:2018-05-31
    标 题 :Stereoselective synthesis of enantiomerically-enriched pantolactone
    发明人:BONRATH WERNER; BOURGEOIS FREDERIC; MEDLOCK JONATHAN; SPARR CHRISTOF
    权利人:DSM IP ASSETS BV
    摘要:The present invention relates stereoselective synthesis of enantiomerically enriched pantolactone.

    专利号:EP-3819295-A1
    优先权日:2019-11-07
    标 题 :Stereoselective synthesis of enantiomerically-enriched pantolactone
    发明人:BONRATH WERNER; BOURGEOIS FREDERIC; MEDLOCK JONATHAN ALAN; SPARR CHRISTOF
    权利人:DSM IP ASSETS BV
    摘要:The present invention relates stereoselective synthesis of enantiomerically enriched pantolactone of formula (I) or (I').

    专利号:EP-0528256-B1
    优先权日:1991-08-12
    标 题:D-2,4-dihydroxy-3,3-dimethylbutyronitrile, its production and use and process for production of D-pantolactone, D-2,4-dihydroxy-3,3-dimethylbutyramide and D-pantothenic acid
    发明人:BEISSWENGER THOMAS DR; HUTHMACHER KLAUS DR; KLENK HERBERT DR
    权利人:DEGUSSA
    摘要:2.1. D-(-)-Pantolactone is an important intermediate in the synthesis of D-(+)-pantothenic acid or D-panthenol and can be obtained from the racemic compound by elaborate racemate resolution methods in the form of pantoic acid salts with chiral auxiliary bases and subsequent resolution of the pairs of salts with subsequent cyclisation of the pantoic acid. Since this synthesis is very elaborate, the object of the present invention is to provide a more suitable intermediate for pantolactone synthesis, which is to be obtainable straightforwardly and at low cost. 2.2. Such an intermediate is D-2,4-dihydroxy-3,3-dimethylbutyronitrile in an optical purity (D:L) of at least 80:20. D-(-)-pantolactone can be prepared in high yields by hydrolysis of the nitrile with concentrated acids. The nitrile is obtainable by reaction of hydroxypivalaldehyde with hydrogen cyanide in the presence of relatively large amounts of a D-oxynitrilase. 2.3. Preparation of D-(-)-pantolactone and D-(+)-pantothenic acid.

    专利号:EP-3748009-A1
    优先权日:2019-06-07
    标 题 :Synthesis of (r)-pantolactone acetate
    发明人:BEKERLE-BOGNER MYRIA; MEDLOCK JONATHAN ALAN; STEINKELLNER GEORG; STROHMEIER GERNOT; STEINER KERSTIN
    权利人:DSM IP ASSETS BV
    摘要:The present invention relates to a 2-step process comprising step (1) kinetic resolution of R/S-pantolactone using an enantioselective acetylating enzyme and step (2) racemization of (S)-pantolactone in the presence of at least one specific chemical catalyst leading to highly enriched (R)-pantolactone acetate. Both step (1) and (2) might be carried-out in a one-pot reaction/system.
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    主要参考文献

    [参考文献]: A D Keefe, Et Al. A Possible Prebiotic Synthesis Of Pantetheine, A Precursor To Coenzyme A. Nature. 1995 Feb 23;373(6516):683-5.
    [参考文献]: A D Keefe, Et Al. Potentially Prebiotic Syntheses Of Condensed Phosphates. Orig Life Evol Biosph. 1996 Feb;26(1):15-25.
    [参考文献]: A Takasu, Et Al. Separation And Determination Of The Enantiomers Of Pantolactone By Gas-Liquid Chromatography. J Chromatogr. 1987 Feb 27;389(1):251-5.
    [参考文献]: Bala Rathinasabapathi, Et Al. Exogenous Supply Of Pantoyl Lactone To Excised Leaves Increases Their Pantothenate Levels. Ann Bot. 2005 May;95(6):1033-7.
    [参考文献]: Cheryl N Miller, Et Al. Pang, A New Ketopantoate Reductase Involved In Pantothenate Synthesis. J Bacteriol. 2013 Mar;195(5):965-76.

    合成参考文献


    摘要:Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D., Pharmaceutical Substances[Online], Thieme: Stuttgart, (2003).
    摘要:Eames, J., Science of Synthesis, (2008) 36, 382.
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