CAS: 80657-57-4; (S)-Methyl 3-Hydroxy-2-Methylpropanoate

该化合物是一个有机化合物,其性能由(S)-前缀在其名称中标明,其特性为:该化合物是异丁酸的衍生物,具有氢氧基组(-OH)和甲基功能组,有助于其在不同溶剂中的再活性和溶性;一般是一种无色的黄色色液体,有香味,可溶于水和有机溶剂,在化学应用中具有多种用途;该化合物经常用于合成药品和农用化学品,并用于生物化学研究,因为其作为代谢途径中的建筑块发挥作用;该化合物的特性可影响其生物活动,使其在药物设计中的立体化学化学学研究中具有重要性;在处理和储存时,应参考安全数据,如任何化学物质,以确保采取适当的预防措施.

结构式图片

相似化合物

42998-03-8 72657-23-9 1910-47-0

欧盟法规

C&L通报

上下游产品

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合成工艺路线路线简述

  • 合成目标产物 Methyl (S)-(+)-3-Hydroxy-2-Methylpropionate 主要起始原料 Methyl 2-(Hydroxymethyl)Acrylate
  • 15484-46-5 = 80657-57-4
    反应条件:1.1 Catalysts: Hydrogen Bromide,Ruthenium,[(1,2,5,6-η)-1,5-Cyclooctadiene]Bis[(1,2,3-η)-2-Methyl-2-Propenyl]-,1,1′-[(5R)-2,2′,3,3′-Tetrahydro[5,5′-Bi-1,4-Benzodioxin]-6,6′-Diyl]Bis[1,1-Diphe... Solvents: Methanol1.2 Reagents: Hydrogen Solvents: Methanol; 23 H,20 Bar,50 °C
    标题:Highly Enantioselective Synthesis Of 3-Hydroxy-2-Methylpropanoic Acid Esters Through Ruthenium-Synphos-Catalyzed Hydrogenation. Useful Building Blocks For The Synthetic Community
    作者:Jeulin,Severine; Et Al
    参考文献:Advanced Synthesis & Catalysis 日期:2007 卷标:349(10) 页码:1592-1596]

    73295-10-0 = 80657-57-4
    反应条件:1.1 Reagents: Potassium Carbonate Solvents: Methanol
    标题:Synthesis Of The S-Enantiomer Of Paniculidine A: Absolute R-Configuration Of The Natural Paniculidines A And B
    作者:Czeskis,B. A.; Et Al
    参考文献:Journal Of The Chemical Society 日期:1989 卷标:(7) 页码:1353-4]

    23953-00-6 = 80657-57-4
    反应条件:1.1 Reagents: Imidazole,Triphenylphosphine,Iodine Solvents: Diethyl Ether,Acetonitrile
    标题:Anomeric C-C Bond Formation Via Sulphones
    作者:Brown,Dearg Sutherland
    参考文献:1990]

    121843-31-0 = 80657-57-4
    反应条件:1.1 Reagents: Sodium Borohydride
    标题:Preparation Of Chiral C5-Building Blocks For Terpene Synthesis By Bakers' Yeast. Reduction Of Sulfur-Functionalized Prenyl Derivatives
    作者:Sato,Toshio; Et Al
    参考文献:Tetrahedron Letters 日期:1988 卷标:29(18) 页码:2197-200]

    110595-22-7 = 80657-57-4
    反应条件:1.1 Reagents: Silica,Permanganic Acid (Hmno4),Potassium Salt (1:1) Solvents: Benzene1.2 Solvents: Diethyl Ether2.1 Reagents: Potassium Carbonate Solvents: Methanol
    标题:Synthesis Of The S-Enantiomer Of Paniculidine A: Absolute R-Configuration Of The Natural Paniculidines A And B
    作者:Czeskis,B. A.; Et Al
    参考文献:Journal Of The Chemical Society 日期:1989 卷标:(7) 页码:1353-4]

    = 80657-57-4
    反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran2.1 Reagents: Triethylamine,4-(Dimethylamino)Pyridine Solvents: Acetic Anhydride2.2 Reagents: Sodium Periodate Catalysts: Ruthenium Trichloride Solvents: Carbon Tetrachloride,Acetonitrile,Water2.3 -2.4 Reagents: Methanol,Potassium Carbonate Solvents: Methanol
    标题:Enantioselective Synthesis Of 1,3-Dioxygen-Substituted Chiral Building Blocks
    作者:Senanayake,Chris H.; Et Al
    参考文献:Synlett 日期:1994 卷标:(3) 页码:199-200]

    = 80657-57-4
    反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran2.1 Reagents: Triethylamine,4-(Dimethylamino)Pyridine Solvents: Acetic Anhydride2.2 Reagents: Sodium Periodate Catalysts: Ruthenium Trichloride Solvents: Carbon Tetrachloride,Acetonitrile,Water2.3 -2.4 Reagents: Potassium Carbonate Solvents: Methanol
    标题:Enantioselective Synthesis Of 1,3-Dioxygen-Substituted Chiral Building Blocks
    作者:Senanayake,Chris H.; Et Al
    参考文献:Synlett 日期:1994 卷标:(3) 页码:199-200]

    121783-34-4 = 80657-57-4
    反应条件:1.1 -2.1 -3.1 Reagents: Sodium Borohydride
    标题:Preparation Of Chiral C5-Building Blocks For Terpene Synthesis By Bakers' Yeast. Reduction Of Sulfur-Functionalized Prenyl Derivatives
    作者:Sato,Toshio; Et Al
    参考文献:Tetrahedron Letters 日期:1988 卷标:29(18) 页码:2197-200]

    599-04-2 + 3156-07-8 = 80657-57-4
    反应条件:1.1 -2.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran3.1 Reagents: Triethylamine,4-(Dimethylamino)Pyridine Solvents: Acetic Anhydride3.2 Reagents: Sodium Periodate Catalysts: Ruthenium Trichloride Solvents: Carbon Tetrachloride,Acetonitrile,Water3.3 -3.4 Reagents: Methanol,Potassium Carbonate Solvents: Methanol
    标题:Enantioselective Synthesis Of 1,3-Dioxygen-Substituted Chiral Building Blocks
    作者:Senanayake,Chris H.; Et Al
    参考文献:Synlett 日期:1994 卷标:(3) 页码:199-200]

    15484-46-5 = 80657-57-4
    反应条件:1.1 Reagents: Hydrogen Catalysts: Rhodium(1+),Bis[(2,3,5,6-η)-Bicyclo[2.2.1]Hepta-2,5-Diene]-,Tetrafluoroborate(...,2-[bis(1-Methylethyl)Phosphino]-1-(11Bs)-Dinaphtho[2,1-D:1′,2′-F][1,3,2]Dioxapho... Solvents: Dichloromethane; 16 H,10 Bar,-40 °C
    标题:Asymmetric Hydrogenation With Highly Active Indolphos-Rh Catalysts: Kinetics And Reaction Mechanism
    作者:Wassenaar,Jeroen; Et Al
    参考文献:Chemistry - A European Journal 日期:2010 卷标:16(22) 页码:6509-6517]

    15484-46-5 = 80657-57-4
    反应条件:1.1 Reagents: Hydrogen Catalysts: Rhodium(1+),Bis[(2,3,5,6-η)-Bicyclo[2.2.1]Hepta-2,5-Diene]-,Tetrafluoroborate(...,2-[bis(1-Methylethyl)Phosphino]-1-(11Bs)-Dinaphtho[2,1-D:1′,2′-F][1,3,2]Dioxapho... Solvents: Dichloromethane; 15 H,20 Bar,-40 °C
    标题:Asymmetric Synthesis Of The Roche Ester And Its Derivatives By Rhodium-Indolphos-Catalyzed Hydrogenation
    作者:Wassenaar,Jeroen; Et Al
    参考文献:Advanced Synthesis & Catalysis 日期:2008 卷标:350(10) 页码:1610-1614]

    74924-27-9 = 80657-57-4
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium,Carbon,Palladium Dihydroxide Solvents: Isopropanol,Tetrahydrofuran; 6 H,Rt
    标题:More Efficient Palladium Catalyst For Hydrogenolysis Of Benzyl Groups
    作者:Li,Yong; Et Al
    参考文献:Synthetic Communications 日期:2006 卷标:36(7) 页码:925-928]

    = 80657-57-4
    反应条件:1.1 Reagents: Potassium Carbonate,Potassium Fluoride Solvents: Methanol,Tetrahydrofuran; 0 °C1.2 Reagents: Hydrogen Peroxide Solvents: Water; 0 °C; 0.5 H,0 °C; 3 H,50 °C1.3 Reagents: 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone Solvents: Dichloromethane,Water; 0 °C; 2 H,0 °C; 0 °C -> Rt1.4 Solvents: Water; Rt
    标题:New Strategies For Protecting Group Chemistry: Synthesis,Reactivity,And Indirect Oxidative Cleavage Of Para-Siletanylbenzyl Ethers
    作者:Tlais,Sami F.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2009 卷标:74(5) 页码:1876-1885]

    143590-14-1 = 80657-57-4
    反应条件:1.1 Reagents: Triethylamine,4-(Dimethylamino)Pyridine Solvents: Acetic Anhydride1.2 Reagents: Sodium Periodate Catalysts: Ruthenium Trichloride Solvents: Carbon Tetrachloride,Acetonitrile,Water1.3 -1.4 Reagents: Potassium Carbonate Solvents: Methanol
    标题:Enantioselective Synthesis Of 1,3-Dioxygen-Substituted Chiral Building Blocks
    作者:Senanayake,Chris H.; Et Al
    参考文献:Synlett 日期:1994 卷标:(3) 页码:199-200]

    19141-40-3 = 80657-57-4
    反应条件:1.1 Reagents: Triethylamine,4-(Dimethylamino)Pyridine Solvents: Acetic Anhydride1.2 Reagents: Sodium Periodate Catalysts: Ruthenium Trichloride Solvents: Carbon Tetrachloride,Acetonitrile,Water1.3 -1.4 Reagents: Methanol,Potassium Carbonate Solvents: Methanol
    标题:Enantioselective Synthesis Of 1,3-Dioxygen-Substituted Chiral Building Blocks
    作者:Senanayake,Chris H.; Et Al
    参考文献:Synlett 日期:1994 卷标:(3) 页码:199-200]

    26543-05-5 = 80657-57-4
    反应条件:1.1 Solvents: Diethyl Ether
    标题:Enantioselective Processes. Reaction Of Optically Active Amines With Photochemically Generated Ketenes
    作者:Schultz,Arthur G.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1984 卷标:49(26) 页码:5202-6]

    = 80657-57-4
    反应条件:1.1 -2.1 Reagents: Sodium Borohydride
    标题:Preparation Of Chiral C5-Building Blocks For Terpene Synthesis By Bakers' Yeast. Reduction Of Sulfur-Functionalized Prenyl Derivatives
    作者:Sato,Toshio; Et Al
    参考文献:Tetrahedron Letters 日期:1988 卷标:29(18) 页码:2197-200]

    27871-49-4 = 80657-57-4
    反应条件:1.1 Reagents: Methyl Iodide,Lithium Hydroxide,Monohydrate,Silver Oxide (Ag2O) Solvents: Tetrahydrofuran,Water2.1 Reagents: Imidazole,Triphenylphosphine,Iodine Solvents: Diethyl Ether,Acetonitrile
    标题:Anomeric C-C Bond Formation Via Sulphones
    作者:Brown,Dearg Sutherland
    参考文献:1990]

    = 80657-57-4
    反应条件:1.1 Reagents: Dabco Solvents: 1,4-Dioxane,Water; 72 H,Rt2.1 Reagents: Glucose,Nadp Catalysts: Nadph-Dehydrogenase Solvents: Water; 24 H,Ph 7.5,Rt
    标题:Biocatalytic Reductions Of Baylis-Hillman Adducts
    作者:Walton,Adam Z.; Et Al
    参考文献:Acs Catalysis 日期:2011 卷标:1(9) 页码:989-993]

    = 80657-57-4
    反应条件:1.1 Reagents: Dabco Solvents: 1,4-Dioxane,Water; Rt2.1 Catalysts: Hydrogen Bromide,Ruthenium,[(1,2,5,6-η)-1,5-Cyclooctadiene]Bis[(1,2,3-η)-2-Methyl-2-Propenyl]-,1,1′-[(5R)-2,2′,3,3′-Tetrahydro[5,5′-Bi-1,4-Benzodioxin]-6,6′-Diyl]Bis[1,1-Diphe... Solvents: Dichloromethane; 0 °C; 30 Min,Rt2.2 Reagents: Hydrogen Solvents: Methanol; 23 H,20 Bar,20 °C
    标题:Convenient General Asymmetric Synthesis Of Roche Ester Derivatives Through Catalytic Asymmetric Hydrogenation: Steric And Electronic Effects Of Ligands
    作者:Pautigny,Cyrielle; Et Al
    参考文献:Advanced Synthesis & Catalysis 日期:2008 卷标:350(16) 页码:2525-2532]

    = 80657-57-4
    反应条件:1.1 Reagents: Dabco Solvents: 1,4-Dioxane; Rt2.1 Reagents: Hydrogen Catalysts: Rhodium(1+),[(1,2,5,6-η)-1,5-Cyclooctadiene][(2R,2′r,5R,5′r)-1,1′-(3,3,4,4-Tetr... Solvents: Tetrahydrofuran; 90 Min,1 Bar,Rt
    标题:Synthesis Of Chiral 2-Hydroxy-1-Methylpropanoates By Rhodium-Catalyzed Stereoselective Hydrogenation Of α-(Hydroxymethyl)Acrylate Derivatives
    作者:Holz,Jens; Et Al
    参考文献:Advanced Synthesis & Catalysis 日期:2008 卷标:350(16) 页码:2533-2543]

    599-04-2 + 134419-96-8 = 80657-57-4
    反应条件:1.1 -2.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran3.1 Reagents: Triethylamine,4-(Dimethylamino)Pyridine Solvents: Acetic Anhydride3.2 Reagents: Sodium Periodate Catalysts: Ruthenium Trichloride Solvents: Carbon Tetrachloride,Acetonitrile,Water3.3 -3.4 Reagents: Potassium Carbonate Solvents: Methanol
    标题:Enantioselective Synthesis Of 1,3-Dioxygen-Substituted Chiral Building Blocks
    作者:Senanayake,Chris H.; Et Al
    参考文献:Synlett 日期:1994 卷标:(3) 页码:199-200]

    84188-96-5 = 80657-57-4
    反应条件:1.1 Reagents: Sucrose,Oxygen Solvents: Water2.1 -3.1 -4.1 Reagents: Sodium Borohydride
    标题:Preparation Of Chiral C5-Building Blocks For Terpene Synthesis By Bakers' Yeast. Reduction Of Sulfur-Functionalized Prenyl Derivatives
    作者:Sato,Toshio; Et Al
    参考文献:Tetrahedron Letters 日期:1988 卷标:29(18) 页码:2197-200
2-(羟甲基)丙烯酸甲酯置于n-Methyl-N-{(S)-1-[2-(Diphenylphosphino)Phenyl]Ethyl}-(S)-1,10-Bi-2-Naphthylphosphoramidite,Bis(1,5-Cyclooctadiene)Rhodium(I) Tetrafluoroborate,氢气体系中,用 二氯甲烷 作为反应溶剂,20.0 °C,1.0 Mpa 条件下,反应 24.0H,反应生成 (S)-(+)-3-羟基异丁酸甲酯
参考文献:手性膦-亚磷酰胺配体经rh催化对映选择性加氢不对称合成手性罗氏酯及其衍生物
标题:手性膦-亚磷酰胺配体经rh催化对映选择性加氢不对称合成手性罗氏酯及其衍生物
摘要:3-羟基-2-甲基丙酸甲酯(称为罗氏酯)是通过rh催化2-羟基甲基丙烯酸甲酯与手性1,2,3,4-甲基丙烯酸的不对称加氢反应而制得的,具有高对映选择性(至96.7%ee).即使在低催化剂负载量(0.1Mol%)下,四氢-1-萘胺衍生的膦-亚磷酰胺配体(thnaphos 5A).对底物范围的研究表明,底物中存在的酯基对对映选择性有显着影响,而具有较大酯基的底物倾向于给出较低的对映选择性.
DOI:10.1016/j.Tetasy.2008.12.026

海关参考信息

专利信息


专利号:US-7348436-B2
优先权日:2004-03-02
标题 :Compounds useful for the synthesis of (+)-discodermolide and methods thereof
发明人:MYLES DAVID C; SHAW SIMON JAMES; SUNDERMANN KURT F
权利人:KOSAN BIOSCIENCES INC
摘要:Compounds and methods useful for the synthesis of (+)-discodermolide, a naturally occurring microtubule stabilizing agent useful as an anti-cancer agent.

专利号:US-4940797-A
优先权日:1989-03-23
标题:Process for synthesis of FK-506 C10-C18 intermediates
发明人:JONES TODD K; MILLS SANDER G; DESMOND RICHARD
权利人:MERCK & CO INC
摘要:A process is described for the improved synthesis of the optically pure C 10 -C 18 fragment of the macrolide structure of the immunosuppressant FK-506. This compound is also useful as an intermediate for preparing FK-506 derivatives.

专利号:US-6384228-B2
优先权日:1998-05-26
标题 :Method for synthesis of halopyridyl-azacyclopentane derivative and intermediate thereof
发明人:NODE MANABU; NAKAMURA DAISAKU; FUJIWARA TOSHIO; ICHIHASHI SHOGO
权利人:NIHON MEDIPHYSICS CO LTD
摘要:The present invention relates to a method for synthesis of an optically active halopyridyl-azacyclo-pentane derivative and the intermediate thereof which comprises preparing an optically active allene-1,3-dicarboxylic acid ester derivative from an optically active acetonedicarboxylic acid ester derivative and then proceeding through a 7-azabicyclo[2.2.1]heptane derivative to obtain the objective product.

专利号:US-7339066-B1
优先权日:2006-05-31
标题 :Intermediates for the synthesis of polypropionate antibiotics
发明人:PARKER KATHLYN; CAO HUANYAN
权利人:UNIV NEW YORK STATE RES FOUND
摘要:The invention relates to intermediate compounds of the formula n nwherein R 1 is H or a protecting group, R 2 and R 3 each independently represent H, methyl, or a leaving group, provided that at least one, but not both, of R 2 and R 3 is a leaving group. The intermediate compounds are useful for the synthesis of discodermolide, its derivatives, and related compounds.

专利号:US-5338865-A
优先权日:1992-03-12
标 题 :Synthesis of halichondrin B and norhalichondrin B
发明人:KISHI YOSHITO; FANG FRANCIS; FORSYTH CRAIG J; SCOLA PAULA M; YOON SUK KYOON
权利人:HARVARD COLLEGE
摘要:Novel chemical compounds that can be used to synthesize halichondrin B and norhalichondrin B, and related derivatives, are described. The synthesis of halichondrin B and norhalichondrin B from these compounds also is described.

专利号:US-7321046-B2
优先权日:2002-09-06
标 题 :Analogs of dictyostatin, intermediates therefor and methods of synthesis thereof
发明人:CURRAN DENNIS P; SHIN YOUSEUNG; FOURNIER JEAN-HUGUES; MANCUSO JOHN; DAY BILLY W; BRUCKNER ARNDT; FUKUI YOSHIKAZU
权利人:UNIV PITTSBURGH
摘要:Dictyostatin and its analogs show great promise as new anticancer agents. The present invention provides dictyostatin analogs, synthetic intermediates for the synthesis of dictyostatin analogs, and synthetic methods for the synthesis of such analogs and intermediates. Dictyostatin analogs can have the following structure or its enantiomer n nwherein R 1 is H, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, or a halogen atom; R 2 is H, a protecting group, an alkyl group, a benzyl group, a trityl group, —SiR a R b R c , CH 2 OR d , or COR e ; R a , R b and R c are independently an alkyl group or an aryl group; R d is an alkyl group, an aryl group, an alkoxylalkyl group, —R i SiR a R b R c or a benzyl group, wherein R i is an alkylene group; R e is an alkyl group, an allyl group, a benzyl group, an aryl group, an alkoxy group, or —NR g R h , wherein R g and R h are independently H, an alkyl group or an aryl group; R 3 is (CH 2 ) n where n is and integer in the range of 0 to 5, —CH 2 CH(CH 3 )—, —CHâ•?CH—, —CHâ•?C(CH 3 )—, or —C≡C—; R 4 isn n nwherein R 23a is H, a protecting group, an alkyl group, a benzyl group, a trityl group, —SiR a R b R c , CH 2 OR d , or COR e ; R 23b is H, a protecting group, an alkyl group, a benzyl group, a trityl group, —SiR a R b R c , CH 2 OR d , or COR e , or R 23a and R 23b together form a portion of six-membered acetal ring incorporating CR t R u ; R t and R u are independently H, an alkyl group, an aryl group or an alkoxyaryl group; and R 5 is H or OR 2b , wherein R 2b is H, a protecting group, an alkyl group, an aryl group, a benzyl group, a trityl group, —SiR a R b R c , CH 2 OR d , or COR e ; provided that the compound is not dictyostatin 1.
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📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

合成参考文献


参考文献:10.1055/s-2007-967978
摘要:Leahy J, Zylstra E, She M, Salamant W. A Flexible Synthetic Approach to the Hennoxazoles. Synlett. 2007 Feb 21;2007(04):0623–7. doi: 10.1055/s-2007-967978.
参考文献:10.1055/s-0032-1318109
摘要:Ley S, Fernández A, Levine Z, Baumann M, Sulzer-Mossé S, Sparr C, Schläger S, Metzger A, Baxendale I. Synthesis of (-)-Hennoxazole A: Integrating Batch and Flow Chemistry Methods. Synlett. 2013 Jan 30;24(04):514–8. doi: 10.1055/s-0032-1318109.
参考文献:10.1055/s-0031-1290675
摘要:Dudley G, Lisboa M, Jeong-Im J, Jones D. Toward a New Palmerolide Assembly Strategy: Synthesis of C16-C24. Synlett. 2012 May 29;23(10):1493–6. doi: 10.1055/s-0031-1290675.
参考文献:10.1055/s-0035-1561469
摘要:Amat M, Bosch J, Llor N, Guignard G. Synthesis of Fluvirucins and Their Aglycons, the Fluvirucinins. Synthesis. 2016 Jun 23;48(17):2705–20. doi: 10.1055/s-0035-1561469.
参考文献:10.1055/s-0033-1340083
摘要:Sabitha G, Gurumurthy C, Yadav J. Studies toward the Synthesis of Iejimalides A–D: Preparation of the C3–11 and C12–C24 Fragments. Synthesis. 2013 Nov 07;46(01):110–8. doi: 10.1055/s-0033-1340083.
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