CAS: 599-04-2; (R)-3-Hydroxy-4,4-Dimethyldihydrofuran-2(3H)-One

该化合物是一个循环酯,是泛甲酸的衍生物(vitamin B.5).它是一种无色的黄色液体,具有略微甜的气味,具有血色,具有血色性质.D-Pantolactone因其湿度特性而在合成各种药品和化妆品方面所发挥的作用而闻名.它具有C6H10O2分子配方,分子重量约为114.14克/摩尔.该化合物溶于水,酒精和其他有机溶剂,具有多种用途.D-Pantolactone可以进行水解,形成D-pantothenical酸,这是生物系统中合成共聚苯丙胺A必不可少的.它在不同条件下的稳定性和再活性使其在有机合成中成为一个重要的中间体.此外,它一般认为在食品和化妆品应用中使用是安全的,尽管由于其化学性质,应当观察适当的处理和安全措施.

结构式图片

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CAS号13031-04-4 二氢-4,4-二甲基-2,3-呋喃二酮 | CAS号133094-78-7 3-(tert-butyldi... | CAS号107730-03-0 (R)-2,4-dihydro... | CAS号924-44-7 乙醛酸乙酯 | CAS号78-84-2 异丁醛 | CAS号1112-33-0 泛醇杂质B | CAS号134929-92-3 (2R)-2,4-dihydr... | CAS号28227-36-3 (R)-2-acetoxy-3... | CAS号17968-81-9 (2R)-2,4-dihydr... | CAS号2545-84-8 Ethanesulfonic ... | CAS号81-13-0 D-泛醇 | CAS号79-83-4 泛酸 | CAS号102096-60-6 (R)-α-丙烯酰基氧基-β,... | CAS号157717-58-3 (S)-3-Azido-4,4... | CAS号79-50-5 DL-泛酰内酯 | CAS号18679-90-8 HOPan | CAS号13861-97-7 Γ-二甲基丁内酯 | CAS号7147-30-0 N-[2-[(5-bromop...

合成工艺路线路线简述

    2,2-二甲基-3-羟基丙醛置于盐酸体系中,用 甲醇,异丙醚,水 作为反应溶剂,化学反应 2.0H,反应生成 D-(-)-泛酰内酯
    参考文献:Calcium Pantothenate. Part 2.1 Optimisation Of Oxynitrilase-Catalysed Asymmetric Hydrocyanation Of 3-Hydroxy-2,2-Dimethylaldehyde: Synthesis Of (R)-Pantolactone
    标题:Calcium Pantothenate. Part 2.1 Optimisation Of Oxynitrilase-Catalysed Asymmetric Hydrocyanation Of 3-Hydroxy-2,2-Dimethylaldehyde: Synthesis Of (R)-Pantolactone
    摘要:The Synthesis Of (R)-Pantolactone Via Oxynitrilase-Catalysed Asymmetric Hydrocyanation Of 3-Hydroxy-2,2-Dimethylaldehyde Has Been Investigated. (R)-Oxynitrilases From Almonds As Well As From Apple And Plum Kernels Were Employed As Catalysts In The Form Of Defatted Meal. A Number Of Factors Influencing The Hydrocyanation Process Have Been Studied And The Conditions Optimised Using Statistical Methods. (R)-Pantolactone With 74% Yield And 30% Ee Has Been Synthesised.
    DOI:10.1021/op050186S

    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:US-4879389-A
    优先权日:1986-06-25
    标题:Chiral phosphinopyrrolidine compounds and their use for asymmetric synthesis of optically active compounds
    发明人:ACHIWA KAZUO
    权利人:ACHIWA KAZUO
    摘要:New chiral phosphinopyrrolidine compounds of the general formula: (I) or (I') wherein R1 is a hydrogen atom, -COR, -COOR, -CONHR or -SO2-R where R is an alkyl or aryl group, R2 and R3 each represents independently an aryl group which may have a substituent or substituents, and R4 and R5 each represents independently an aliphatic or cycloaliphatic hydrocarbyl group which may have a substituent or substituents, as well as the use of these compounds as ligand for a metal complex catalyst for asymmetric synthesis of optically active compounds. The new chiral phosphinopyrrolidine compounds are useful ligands which attain both of high optical yield and high reaction efficiency in catalytic asymmetric reduction.

    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:US-4985567-A
    优先权日:1988-03-07
    标题:Chiral phosphinopyrrolidine compounds and their use for asymmetric synthesis of optically active compounds
    发明人:ACHIWA KAZUO; TAKEDA HIDEO
    权利人:KAZUO ACHIWA; FUJI YAKUHIN KOGYO KK
    摘要:New chiral phosphinopyrrolidine compounds of the general formula: ##STR1## wherein R 1 is hydrogen or --COA 1 , --COOA 2 , --CONHA 3 , --SO 2 A 4 or --PO(A 5 ) 2 , A 1 , A 2 , A 3 , A 4 and A 5 each represents independently alkyl or aryl, R 2 is phenyl, di(lower-alkyl)aminophenyl, lower-alkoxyphenyl or 3,5-dimethyl-4-methoxyphenyl, and R 3 is phenyl, lower-alkylphenyl, di(lower-alkyl)aminophenyl, lower-alkoxyphenyl or 3,5-dimethyl-4-methoxyphenyl, with the proviso that R 2 and R 3 may not simultaneously by phenyl, p-di(lower-alkyl)-aminophenyl or p-lower-alkoxyphenyl, as well as the use of these compounds as ligand for a metal complex catalyst for asymmetric synthesis of optically active compounds. The new chiral phosphinopyrrolidine compounds are useful ligands which attain both of high optical yield and high reaction efficiency in catalytic asymmetric reduction.
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    主要参考文献


    1: Heidlindemann M, Hammel M, Scheffler U, Mahrwald R, Hummel W, Berkessel A, Gröger H. Chemoenzymatic synthesis of vitamin B5-intermediate (R)-pantolactone via combined asymmetric organo- and biocatalysis. J Org Chem. 2015 Apr 3;80(7):3387-96. doi: 10.1021/jo502667x. Epub 2015 Mar 23. doi: 10.1021/jo101782q. Epub 2010 Dec 31. Russian. Chinese. French. doi: 10.1128/JB.01740-12. Epub 2012 Dec 14.
    15: Ball M, Baron A, Bradshaw B, Dumeunier R, O'Brien M, Thomas EJ. The evolution of a stereoselective synthesis of the C1-C16 fragment of bryostatins. Org Biomol Chem. 2016 Oct 12;14(40):9650-9681. doi: 10.1016/j.foodchem.2015.07.091. Epub 2015 Jul 23. doi: 10.1021/am504702p. Epub 2014 Oct 21. doi: 10.5402/2012/161890. Print 2012.
    19: Kashinath K, Jadhav PD, Reddy DS. Total synthesis of an anticancer norsesquiterpene alkaloid isolated from the fungus Flammulina velutipes. Org Biomol Chem. 2014 Jun 28;12(24):4098-103. doi: 10.1039/c4ob00300d. doi: 10.1016/j.chroma.2013.12.078. Epub 2014 Jan 2.

    合成参考文献


    摘要:Yamashita, Y.; Gröger, H., Science of Synthesis, (2019) , 346.
    参考文献:10.1007/bf01388170
    摘要:Calmes M, Daunis J. How to build optically active alpha-amino acids. Amino Acids. 1999;16(3-4):215–50. doi: 10.1007/bf01388170.
    参考文献:10.1007/bf01388176
    摘要:Bouifraden S, Drouot C, el Hadrami M, Guenoun F, Lecointe L, Mai N, Paris M, Pothion C, Sadoune M, Sauvagnat B, Amblard M, Aubagnac JL, Calmes M, Chevallet P, Daunis J, Enjalbal C, Fehrentz JA, Lamaty F, Lavergne JP, Lazaro R, Rolland V, Roumestant ML, Viallefont P, Vidal Y, Martinez J. Some of the amino acid chemistry going on in the Laboratory of Amino Acids, Peptides and Proteins. Amino Acids. 1999;16(3-4):345–79. doi: 10.1007/bf01388176.
    参考文献:10.1128/jb.01740-12
    摘要:Miller CN, LoVullo ED, Kijek TM, Fuller JR, Brunton JC, Steele SP, Taft-Benz SA, Richardson AR, Kawula TH. PanG, a New Ketopantoate Reductase Involved in Pantothenate Synthesis. Journal of Bacteriology. 2012 Dec 14;195(5):965–76. doi: 10.1128/jb.01740-12.
    参考文献:10.1007/s13197-021-05093-6
    摘要:Tadi SRR, Nehru G, Limaye AM, Sivaprakasam S. High-level expression and optimization of pantoate-β-alanine ligase in Bacillus megaterium for the enhanced biocatalytic production of D-pantothenic acid. Journal of Food Science and Technology. 2021 Apr 20;59(3):917–26. doi: 10.1007/s13197-021-05093-6.
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