CAS: 79893-89-3; (2S,3R)-Methyl 2-Benzamido-3-Hydroxybutanoate

该化合物是L-threonine的一种受保护的衍生物,通常用于peptide合成和有机化学研究.Benzyl(Bz)组在混合反应中为氨酸提供了稳定性,而甲基酯(OMe)增加了有机溶剂的溶解性.该化合物因其与标准保护群体战略的兼容性,在固相浸化物合成(SPPS)中特别宝贵.它受控制的再活动允许有选择地去保护和延长peptide链.Bz-Thr-OMe也用于酶-substels的相互作用研究,并用作改良的peptid的建筑块.建议在水下进行适当处理以保持其完整性.

结构式图片

相似化合物

2901-80-6 60538-16-1 27696-01-1

物理性质

MSDS等安全信息

上下游产品

CAS号39994-75-7 L-苏氨酸甲酯盐酸盐 | CAS号98-88-4 苯甲酰氯 | CAS号3373-59-9 L-苏氨酸甲酯 | CAS号186581-53-3 重氮甲烷 | CAS号27696-01-1 N-苯甲酰基-L-苏氨酸 | CAS号100063-41-0 5-Methyl-2-phen... | CAS号55-21-0 苯甲酰胺 | CAS号18735-74-5 5-甲基-2-苯基-1,3--... | CAS号77320-41-3 methyl 2-benzam...

合成工艺路线路线简述

  • 72-19-5 + 98-88-4 = 79893-89-3
    反应条件:1.1 Reagents: Thionyl Chloride Solvents: Methanol; 0 - 15 °C; 30 Min,0 - 15 °C; 20 H,> 15 °C1.2 Reagents: Sodium Bicarbonate Solvents: 1,4-Dioxane,Water; 0 °C; 10 - 15 °C; 20 Min,10 - 15 °C; 3 H,> 15 °C
    标题:Synthesis And Evaluation Of In Vivo Anti-Hypothermic Effect Of All Stereoisomers Of The Thyrotropin-Releasing Hormone Mimetic: Rovatirelin Hydrate
    作者:Kobayashi,Naotake; Et Al
    参考文献:Journal Of Peptide Science 日期:2019 卷标:25(12)]

    72-19-5 = 79893-89-3
    反应条件:1.1 Reagents: Thionyl Chloride Solvents: Methanol; Cooled; 10 Min,4 °C; 4 °C -> 22 °C; 2 H,Reflux2.1 Reagents: Triethylamine Solvents: Dichloromethane; 15 Min,4 °C; 2 H,4 °C
    标题:Rationally Designed Amanitins Achieve Enhanced Cytotoxicity
    作者:Todorovic,Mihajlo; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2022 卷标:65(15) 页码:10357-10376]

    72-19-5 = 79893-89-3
    反应条件:1.1 Reagents: Hydrochloric Acid; Reflux2.1 Reagents: Triethylamine Solvents: Methanol; Rt
    标题:The Synthesis Of Novel Chiral Ferrocenyl Aziridino Alcohol Ligands With Two Stereogenic Carbons And Structural Characteristics
    作者:Wang,Qian; Et Al
    参考文献:Advanced Materials Research (Durnten-Zurich 日期:2012 卷标:518 页码:518-523]

    1138-80-3 + 79893-89-3 = 79893-89-3 + 1212-53-9
    反应条件:1.1 Reagents: Dicyclohexylcarbodiimide,4-(Dimethylamino)Pyridine Solvents: Dichloromethane2.1 Reagents: Sodium Hydroxide Solvents: Methanol2.2 Reagents: Diazomethane
    标题:Synthesis Of An Actinomycin-Related Peptide Lactone From The Corresponding Cyclic Pentapeptide By N,O-Acyl Shift
    作者:Mauger,Anthony B.; Et Al
    参考文献:International Journal Of Peptide & Protein Research 日期:1989 卷标:34(3) 页码:196-9]

    39994-75-7 + 98-88-4 = 79893-89-3
    反应条件:1.1 Reagents: Triethylamine Solvents: Dichloromethane; 0 °C; 0 °C -> Rt; 3 H,Rt
    标题:Modular Phosphite-Oxazoline/oxazine Ligand Library For Asymmetric Pd-Catalyzed Allylic Substitution Reactions: Scope And Limitations-Origin Of Enantioselectivity
    作者:Dieguez,Montserrat; Et Al
    参考文献:Chemistry - A European Journal 日期:2008 卷标:14(12) 页码:3653-3669]

    39994-75-7 + 98-88-4 = 79893-89-3
    反应条件:1.1 Reagents: Triethylamine Solvents: Dichloromethane; 30 Min,0 °C; Overnight,0 °C -> Rt1.2 Reagents: Citric Acid Solvents: Water; Rt
    标题:Synthesis Of 2-Oxazolines By In Situ Desilylation And Cyclodehydration Of β-Hydroxyamides
    作者:Brandstatter,Marco; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2015 卷标:80(1) 页码:40-51]

    98-88-4 + 3373-59-9 = 79893-89-3
    反应条件:1.1 Reagents: Triethylamine Solvents: Dichloromethane; 12 H,0 °C1.2 Reagents: Water; 0 °C
    标题:New Dihydroxy Bis(Oxazoline) Ligands For The Palladium-Catalyzed Asymmetric Allylic Alkylation: Experimental Investigations Of The Origin Of The Reversal Of The Enantioselectivity
    作者:Ait-Haddou,Hassan; Et Al
    参考文献:Chemistry - A European Journal 日期:2004 卷标:10(3) 页码:699-707]

    98-88-4 + 3373-59-9 = 79893-89-3
    反应条件:1.1 Reagents: Triethylamine Solvents: Dichloromethane; 0 °C; 12 H,Rt1.2 Reagents: Sodium Bicarbonate Solvents: Water
    标题:Synthesis Of 2-Oxazolines And Related N-Containing Heterocycles Using [et2Nsf2]Bf4 As A Cyclodehydration Agent
    作者:Pouliot,Marie-France; Et Al
    参考文献:Tetrahedron Letters 日期:2012 卷标:53(32) 页码:4121-4123]

    98-88-4 + 3373-59-9 = 79893-89-3
    反应条件:1.1 Reagents: Triethylamine Solvents: Dichloromethane; 15 Min,4 °C; 2 H,4 °C
    标题:Rationally Designed Amanitins Achieve Enhanced Cytotoxicity
    作者:Todorovic,Mihajlo; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2022 卷标:65(15) 页码:10357-10376]

    39994-75-7 + 65-85-0 = 79893-89-3
    反应条件:1.1 Reagents: 1-Hydroxybenzotriazole,Diisopropylethylamine,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Solvents: Dichloromethane; 5 D,Rt1.2 Reagents: Ammonium Chloride Solvents: Water
    标题:The Rapid Synthesis Of Oxazolines And Their Heterogeneous Oxidation To Oxazoles Under Flow Conditions
    作者:Glockner,Steffen; Et Al
    参考文献:Organic & Biomolecular Chemistry 日期:2015 卷标:13(1) 页码:207-214]

    72-19-5 + 98-88-4 = 79893-89-3
    反应条件:1.1 Reagents: Thionyl Chloride Solvents: Methanol; Cooled; 10 Min,4 °C; 4 °C -> 22 °C; 2 H,Reflux1.2 Reagents: Triethylamine Solvents: Dichloromethane; 15 Min,4 °C; 2 H,4 °C
    标题:Rationally Designed Amanitins Achieve Enhanced Cytotoxicity
    作者:Todorovic,Mihajlo; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2022 卷标:65(15) 页码:10357-10376]

    65-85-0 + 3373-59-9 = 79893-89-3
    反应条件:1.1 Solvents: Tetrahydrofuran; 15 Min,Rt1.2 Reagents: 4-(4,6-Dimethoxy-1,3,5-Triazin-2-Yl)-4-Methylmorpholinium Chloride; 3 H,Rt
    标题:Phosphorus-Based Organocatalysis For The Dehydrative Cyclization Of N-(2-Hydroxyethyl)Amides Into 2-Oxazolines
    作者:Soleymani Movahed,Farzaneh; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2022 卷标:87(1) 页码:243-257]

    62076-66-8 + 98-88-4 = 79893-89-3
    反应条件:1.1 Reagents: Diisopropylethylamine Solvents: Dichloromethane; 0 °C; 1 H,0 °C
    标题:In Situ Assembly And Screening Of Enzyme Inhibitors With Surface-Tension Microarrays
    作者:Mugherli,Laurent; Et Al
    参考文献:Angewandte Chemie 日期:2009 卷标:48(41) 页码:7639-7644]

    77320-41-3 = 79893-89-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Ruthenium(1+),[1,1′-[(1R,4R)-1,4-Dimethyl-2-Butene-1,4-Diyl]Bis[1,1-Diphenylpho... Solvents: Methanol,Dichloromethane; 24 H,Rt
    标题:Chiral 1,4-Bis-Diphosphine Ligands From Optically Active (Z)-Olefins
    作者:Cesarotti,Edoardo; Et Al
    参考文献:Tetrahedron: Asymmetry 日期:2007 卷标:18(11) 页码:1278-1283]

    72-19-5 = 79893-89-3
    反应条件:1.1 Reagents: Thionyl Chloride Solvents: Methanol; 0 - 15 °C; 30 Min,0 - 15 °C; 20 H,> 15 °C2.1 Reagents: Sodium Bicarbonate Solvents: 1,4-Dioxane,Water; 0 °C; 10 - 15 °C; 20 Min,10 - 15 °C; 3 H,> 15 °C
    标题:Synthesis And Evaluation Of In Vivo Anti-Hypothermic Effect Of All Stereoisomers Of The Thyrotropin-Releasing Hormone Mimetic: Rovatirelin Hydrate
    作者:Kobayashi,Naotake; Et Al
    参考文献:Journal Of Peptide Science 日期:2019 卷标:25(12)]

    = 79893-89-3 + 1212-53-9
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Methanol1.2 Reagents: Diazomethane
    标题:Synthesis Of An Actinomycin-Related Peptide Lactone From The Corresponding Cyclic Pentapeptide By N,O-Acyl Shift
    作者:Mauger,Anthony B.; Et Al
    参考文献:International Journal Of Peptide & Protein Research 日期:1989 卷标:34(3) 页码:196-9]

    98-88-4 + 41961-03-9 = 79893-89-3 + 1212-53-9
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane1.2 Reagents: Sodium Acetate Solvents: 1,4-Dioxane,Water2.1 Reagents: Sodium Hydroxide Solvents: Methanol2.2 Reagents: Diazomethane
    标题:Synthesis Of An Actinomycin-Related Peptide Lactone From The Corresponding Cyclic Pentapeptide By N,O-Acyl Shift
    作者:Mauger,Anthony B.; Et Al
    参考文献:International Journal Of Peptide & Protein Research 日期:1989 卷标:34(3) 页码:196-9
📜(+/-)-5T-Methyl-2-Phenyl-4,5-Dihydro-Oxazole-4R-Carboxylic Acid置于盐酸,乙醚,马钱子碱体系中,化学反应生成 N-苯甲酰-L-苏氨酸甲酯
参考文献:15.L-苏氨酸的制备.四种立体异构体α-氨基-β-羟基丁酸的相互转化
标题:15.L-苏氨酸的制备.四种立体异构体α-氨基-β-羟基丁酸的相互转化
摘要:
DOI:10.1039/jr9500000062

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合成参考文献


参考文献:10.1007/bf01388169
摘要:Miyazawa T. Enzymatic resolution of amino acids via ester hydrolysis. Amino Acids. 1999;16(3-4):191–213. doi: 10.1007/bf01388169.
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