CAS: 96886-55-4; (S)-2-Amino-2-Methylpent-4-Enoic Acid

该化合物是一种非蛋白性α-氨酸,在C-2位置上有一个手性中心,并有一个不饱和的pent-4-蛋白侧链,其立体特性(S)配置确保了高对等纯度,使其在不对称合成和peptide改变中具有价值.α-碳的甲基组会增强不耐烦性障碍,影响peptide设计中的相容稳定性.终端烷会通过点击化学或交叉组合反应为进一步功能化提供反应式处理器.该化合物在药用化学中特别有用,可以进行酶基基体相互作用,或作为生物活性分子的建筑块.其结构多功能性和合成可及可获取性使得它成为对乳房术和乳房辅助剂研究的一个实用选择.

结构式图片

相似化合物

288617-76-5 288617-71-0 96886-56-5

物理性质

MSDS等安全信息

欧盟法规

ECHA物质C&L通报

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CAS号213619-63-7 (3S,6R)-3-allyl... | CAS号53933-42-9 2-(benzylidene-... | CAS号106-95-6 烯丙基溴

合成工艺路线路线简述

  • 898823-65-9 = 96886-55-4
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Methanol,Acetone; 2 H,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 3 - 4,Rt -> 0 °C1.3 Reagents: Hydrochloric Acid Solvents: Water; 3 H,92 °C1.4 Reagents: (+/-)-Propylene Oxide Solvents: Ethanol; 1 H,Rt
    标题:Asymmetric Synthesis Of α,α-Disubstituted α-Amino Acids By Diastereoselective Alkylation Of Camphor-Based Tricyclic Iminolactone
    作者:Xu,Peng-Fei; Li,Shuo; Lu,Ta-Jung; Wu,Chen-Chang; Fan,Botao; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2006 卷标:71(12) 页码:4364-4373]

    = 96886-55-4
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol1.2 -
    标题:Asymmetric Synthesis Of Bis(α-Methylamino Acid) Via A Bpb-Ni(Ii)-Ala Complex
    作者:Ye,Lingya; Wu,Hongli; Zhang,Xiaolong; Zhou,Jiadong; Cao,Fei; Et Al
    参考文献:Youji Huaxue 日期:2009 卷标:29(8) 页码:1282-1286]

    = 96886-55-4
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol
    标题:Asymmetric Synthesis Of γ-Unsaturated Amino Acids Using Chiral Auxiliary
    作者:Ye,Ling-Ya; Wu,Hong-Li; Zhang,Xiao-Long; Zhou,Jia-Dong; Cao,Fei; Et Al
    参考文献:Yingyong Huaxue 日期:2009 卷标:26(3) 页码:346-348]

    191284-36-3 = 96886-55-4
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Tetrahydrofuran,Water1.2 Reagents: Lithium Hydroxide Solvents: Tetrahydrofuran,Water
    标题:Asymmetric Synthesis Of α-Methyl α-Amino Acids By Diastereoselective Alkylation Of Optically Active 6-Isopropyl-3-Methyl-2,3-Dihydro-6H-1,4-Oxazin-2-Ones
    作者:Chinchilla,Rafael; Falvello,Larry R.; Galindo,Nuria; Najera,Carmen
    参考文献:Angewandte Chemie 日期:1997 卷标:36(9) 页码:995-997]

    1318776-55-4 = 96886-55-4
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; Rt; Rt -> 0 °C1.2 Reagents: Bromine; 0 °C; 0 °C; 0 °C -> 75 °C; 4 H,75 °C1.3 Reagents: Hydrochloric Acid Solvents: Water; Neutralized
    标题:Microbial Whole Cell-Catalyzed Desymmetrization Of Prochiral Malonamides: Practical Synthesis Of Enantioenriched Functionalized Carbamoylacetates And Their Application In The Preparation Of Unusual α-Amino Acids
    作者:Zhang,Li-Bin; Wang,De-Xian; Wang,Mei-Xiang
    参考文献:Tetrahedron 日期:2011 卷标:67(31) 页码:5604-5609]

    = 96886-55-4 [标题:Reaction Conditions
    标题:Synthesis Of Modified Partial Structures Of The Bacterial Cell Wall. 2. Retarded Metabolism Of Lipopeptides By Insertion Of α-Substituted α-Amino Acids
    作者:Frauer,Alexandra; Mehlfuehrer,Michaela; Thirring,Klaus; Berner,Heinz
    参考文献:Journal Of Organic Chemistry 日期:1994 卷标:59(15) 页码:4215-22]

    = 96886-55-4 [标题:Reaction Conditions
    标题:(S)-2-[n-(N'-Benzylprolyl)Amino]Benzophenone (Bpb) - A Reagent For The Synthesis Of Optically Pure α-Amino Acids
    作者:Belokon,I.
    参考文献:Janssen Chimica Acta 日期:1992 卷标:10(2) 页码:4-12]

    1443008-01-2 = 96886-55-4 + 90365-73-4
    反应条件:1.1 Solvents: 1,4-Dioxane,Water; 1 H,100 °C
    标题:Synthesis Of Quaternary α-Methyl α-Amino Acids By Asymmetric Alkylation Of Pseudoephenamine Alaninamide Pivaldimine
    作者:Hugelshofer,Cedric L.; Mellem,Kevin T.; Myers,Andrew G.
    参考文献:Organic Letters 日期:2013 卷标:15(12) 页码:3134-3137]

    = 96886-55-4 + 12093-10-6
    反应条件:1.1 Reagents: Amberlyst 15 Solvents: Acetone,Water; 16 H,Ph 2 - 4,Rt1.2 Reagents: Ammonia Solvents: Water; Rt
    标题:Stereoselective Functionalisation Of Cis- And Trans-2-Ferrocenyl-3-Pivaloyl-4-Alkyl-1,3-Oxazolidin-5-Ones: Asymmetric Synthesis Of (R)- And (S)-2-Alkyl-2-Aminopent-4-Enoic Acids And (2R,3S)-2-Amino-2-Methyl-3-Hydroxy-3-Phenylpropanoic Acid
    作者:Alonso,Francisco; Davies,Stephen G.; Elend,Almut S.; Leech,Michael A.; Roberts,Paul M.; Et Al
    参考文献:Organic & Biomolecular Chemistry 日期:2009 卷标:7(3) 页码:527-536]

    = 96886-55-4 + 96293-17-3
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Ethanol,Water
    标题:Asymmetric Synthesis Of α-Methyl Amino Acids Via Alkylation Of Glycine,Alanine And Phenylalanine In Chiral Nickel(Ii) Complexes
    作者:Belokon,Yu. N.; Chernoglazova,N. I.; Bakhmutov,V. I.; Garbalinskaya,N. S.; Belikov,V. M.
    参考文献:Izvestiya Akademii Nauk Sssr 日期:1987 卷标:(12) 页码:2798-804]

    = 96886-55-4 + 96886-56-5
    反应条件:1.1 Reagents: Hydrochloric Acid,Water Solvents: Water
    标题:Preparation Of Optically Pure α-Methyl-α-Amino Acids Via Alkylation Of The Nickel(Ii) Schiff Base Of (R,S)-Alanine With (S)-2-N-(N'-Benzylprolyl)Aminobenzaldehyde
    作者:Belokon,Y. N.; Chernoglazova,N. I.; Kochetkov,C. A.; Garbalinskaya,N. S.; Belikov,V. M.
    参考文献:Journal Of The Chemical Society 日期:1985 卷标:(1985) 页码:171-2]

    206184-21-6 = 96886-55-4
    反应条件:1.1 Reagents: Sodium Hydroxide Catalysts: (S,S)-Taddol Solvents: Toluene1.2 -
    标题:Asymmetric Ptc C-Alkylation Catalyzed By Chiral Derivatives Of Tartaric Acid And Aminophenols. Synthesis Of (R)- And (S)-α-Methyl Amino Acids
    作者:Belokon,Yuri N.; Kochetkov,Konstantin A.; Churkina,Tatiana D.; Ikonnikov,Nikolai S.; Chesnokov,Alexey A.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2000 卷标:65(21) 页码:7041-7048]

    88820-87-5 = 96886-55-4
    反应条件:1.1 Solvents: Water
    标题:A Practical Asymmetric Synthesis Of α-Methyl α-Amino Acids Using A Chiral Cu-Salen Complex As A Phase Transfer Catalyst
    作者:Belokon,Y. N.; Davies,R. G.; North,M.
    参考文献:Tetrahedron Letters 日期:2000 卷标:41(37) 页码:7245-7248]

    = 96886-55-4
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water; > 1 Min,20 - 60 °C
    标题:Rapid Asymmetric Synthesis Of Amino Acids Via Niii Complexes Based On New Fluorine Containing Chiral Auxiliaries
    作者:Saghyan,Ashot S.; Dadayan,Ani S.; Dadayan,Slavik A.; Mkrtchyan,Anna F.; Geolchanyan,Arpine V.; Et Al
    参考文献:Tetrahedron: Asymmetry 日期:2010 卷标:21(24) 页码:2956-2965]

    = 96886-55-4
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Dimethylformamide; 60 Min,45 - 50 °C1.2 Reagents: Acetic Acid Solvents: Water; Neutralized1.3 Reagents: Hydrochloric Acid Solvents: Methanol,Water; 50 °C
    标题:New Chiral Niii Complexes Of Schiff'S Bases Of Glycine And Alanine For Efficient Asymmetric Synthesis Of α-Amino Acids
    作者:Saghiyan,Ashot S.; Dadayan,Slavik A.; Petrosyan,Satenik G.; Manasyan,Luisa L.; Geolchanyan,Arpine V.; Et Al
    参考文献:Tetrahedron: Asymmetry 日期:2006 卷标:17(3) 页码:455-467]

    213619-63-7 = 96886-55-4
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Acetic Acid,Toluene1.2 Solvents: Ethanol1.3 Reagents: Ammonia Solvents: Water
    标题:Asymmetric Synthesis Of α-Methyl α-Amino Acids Through Diastereoselective Alkylation Under Mild Reaction Conditions Of An Iminic Alanine Template With A 1,2,3,6-Tetrahydro-2-Pyrazinone Structure
    作者:Najera,Carmen; Abellan,Tomas; Sansano,Jose M.
    参考文献:European Journal Of Organic Chemistry 日期:2000 卷标:(15) 页码:2809-2820]

    191284-36-3 = 96886-55-4
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Water; 1 H,Rt1.2 Reagents: Lithium Hydroxide Solvents: Tetrahydrofuran,Water; 6 H,Rt
    标题:New Oxazinone And Pyrazinone Derivatives As Chiral Reagents For The Asymmetric Synthesis Of α-Amino Acids
    作者:Abellan,Tomas; Chinchilla,Rafael; Galindo,Nuria; Najera,Carmen; Sansano,Jose M.
    参考文献:Journal Of Heterocyclic Chemistry 日期:2000 卷标:37(3) 页码:467-479]

    = 96886-55-4 [标题:Reaction Conditions
    标题:Product Subclass 7: 2-Aminoalkanoic Acids (α-Amino Acids)
    作者:Wolkenberg,S. E.; Garbaccio,R. M.
    参考文献:Science Of Synthesis 日期:2006 卷标:20 页码:385-482]

    = 96886-55-4
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Water
    标题:General Method For The Asymmetric Synthesis Of α-Amino Acids Via Alkylation Of The Chiral Nickel(Ii) Schiff Base Complexes Of Glycine And Alanine
    作者:Belokon,Yu. N.; Bakhmutov,V. I.; Chernoglazova,N. I.; Kochetkov,K. A.; Vitt,S. V.; Et Al
    参考文献:Journal Of The Chemical Society 日期:1988 卷标:(2) 页码:305-12]

    = 96886-55-4 [标题:Reaction Conditions
    标题:Synthesis Of (Optically Active) Sulfur-Containing Trifunctional Amino Acids By Radical Addition To (Optically Active) Unsaturated Amino Acids
    作者:Broxterman,Quirinus B.; Kaptein,Bernard; Kamphuis,Johan; Schoemaker,Hans E.
    参考文献:Journal Of Organic Chemistry 日期:1992 卷标:57(23) 页码:6286-94]

    1266681-06-4 = 96886-55-4 + 36482-69-6
    反应条件:1.1 Reagents: Cesium Hydroxide Solvents: Water; 2 H,70 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; Rt
    标题:Asymmetric Synthesis Of α-Methyl-α-Amino Acids Via Diastereoselective Alkylation Of (1S)-(+)-3-Carene Derived Tricyclic Iminolactone
    作者:Lu,Ta-Jung; Lin,Cheng-Kun
    参考文献:Journal Of Organic Chemistry 日期:2011 卷标:76(6) 页码:1621-1633]

    144125-67-7 = 96886-55-4 + 144072-99-1
    反应条件:1.1 Catalysts: Aminopeptidase Solvents: Water
    标题:Enzymic Resolution Of α,α-Disubstituted α-Amino Acid Esters And Amides
    作者:Kaptein,Bernard; Boesten,Wilhelmus H. J.; Broxterman,Quirinus B.; Peters,Piet J. H.; Schoemaker,Hans E.; Et Al
    参考文献:Tetrahedron: Asymmetry 日期:1993 卷标:4(6) 页码:1113-16
📜(2R,4S)-2-Ferrocenyl-3-Pivaloyl-4-Allyl-4-Methyl-1,3-Oxazolidin-5-One置于amberlyst-15 Resin体系中,用 水,丙酮 作为反应溶剂,化学反应 16.0H,以77%的收率获得产物(S)-(-)-α-烯丙基丙氨酸
参考文献:立体选择性官能化的顺式和反式-2-二茂铁基-3-新戊基-4-烷基-1,3-恶唑烷丁-5-酮:(R)-和(S)-2-烷基-2-氨基戊基-的不对称合成4-烯酸和(2 R,3 S)-2-氨基-2-甲基-3-羟基-3-苯基丙酸†
标题:立体选择性官能化的顺式和反式-2-二茂铁基-3-新戊基-4-烷基-1,3-恶唑烷丁-5-酮:(R)-和(S)-2-烷基-2-氨基戊基-的不对称合成4-烯酸和(2 R,3 S)-2-氨基-2-甲基-3-羟基-3-苯基丙酸†
摘要:用lda处理一系列顺式和反式-2-二茂铁基-3-新戊酰基-4-烷基-1,3-恶唑烷-5-酮,然后加入烯丙基溴促进在恶唑烷酮环的4-位抗立体定向2-二茂铁基的高度立体选择性烯丙基化(> 98%de).所得4,4-二取代的恶唑烷酮(> 98%de)的水解在高ee中产生对映体(R)-和(S)-2-烷基-2-氨基戊-4-烯酸.此外,顺式-2-二茂铁基-3-新戊酰基-4-甲基-1,3-恶唑烷-5-苯甲醛然后原位进行o-保护得到> 98%de的o-保护的羟醛产物,并进行水解(2 R,3 S)-2-氨基-2-甲基-3-羟基-3-苯基丙酸 在> 98%de.
DOI:10.1039/b814453B

海关参考信息

专利信息


专利号:US-7060818-B2
优先权日:2003-02-21
标题:Synthesis of macrocyclic tetraamido compounds and new metal insertion process
发明人：HORWITZ COLIN P; GHOSH ANINDYA
权利人:UNIV CARNEGIE MELLON
摘要:An improved method of synthesizing a macrocyclic tetraamido compound includes protecting the amino portion of an amino carboxylic acid to form a protected amino carboxylic acid; exposing the protected amino carboxylic acid to a first solvent, preferably a hydrocarbon solvent, such as toluene or 1,2-dichloroethane, dichloromethane, dibromomethane and 1,2-dibromoethane. The carboxylic acid portion of the protected amino carboxylic acid is then converted to an activated carboxylic acid by one of esterification or acid halide formation, to form a protected amino activated carboxylic acid derivative. The protected amino activated carboxylic acid derivative is reacted with a diamine in the presence of a second solvent, such as THF or ,2-dichloroethane, dichloromethane, dibromomethane and 1,2-dibromoethane, to form a protected diamide diamine intermediate. Following deprotection, the diamide diamine intermediate is reacted with an activated diacid, such as an activated malonate, oxalate or succinate derivative to form the macrocyclic tetraamido compound. The macrocyclic tetraamido compound may further be complexed with a transition metal.

专利号:WO-2004101476-A1
优先权日:2003-05-16
标题:Metathesis reaction involving the unsaturated side chain of an alpha, alpha-disubstituted amino acid
发明人：RUTJES FLORIS PETRUS JOHANNES; STORCKEN ROY PETRUS MARIA; BROXTERMAN QUIRINUS BERNARDUS; KAPTEIN BERNARDUS
权利人:DSM IP ASSETS BV; RUTJES FLORIS PETRUS JOHANNES; STORCKEN ROY PETRUS MARIA; BROXTERMAN QUIRINUS BERNARDUS; KAPTEIN BERNARDUS
摘要:The invention relates to a process for amino acid synthesis, i.e., the preparation of side chain unsaturated α,α-disubstituted-α-amino acid derivatives with formula (1) wherein: * denotes a stereogenic C-atom PG represents an N-protecting group or the C-terminal part of an optionally protected amino acid or peptide chain; X represents an optionally substituted amine group or an alkoxy group; R1 represents an optionally substituted alkyl group; Ri represents R2 or R3; if Ri = R2 then Rii = R5 and if Ri = R3 then Rii = H; R2, R3 and R5 each independently represent H, an optionally substituted (cyclo)alkyl, (hetero)aryl, acyl, alkoxycarbonyl, cyano, di-alkylphosphonyl, oxiranyl group, a CHO group optionally protected as its acetal, or a group derived from an O-protected carbohydrate, or R2 and R5 may form together with the C-atorn to which they are attached an optionally substituted hydrocarbon ring, with the proviso that R2 , R3 and R5 do not all represent H at the same time. R4 represents H, an alkyl group or an aryl group; n represents an integer larger than or equal to 0, via a cross metathesis reaction between the corresponding amino acid derivative precursor and an (eventually substituted) alkene.

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合成参考文献


摘要:Hall, M.; Faber, K.; Tasnádi, G., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 1, 307.
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