CAS: 91229-86-6; (S)-Tert-Butyl 5-Bromo-2-((Tert-Butoxycarbonyl)Amino)Pentanoate

该化合物是一种在有机合成中广泛使用的手性中间体,特别是在浸泡物化学和制药应用中.该化合物的特点是一个叔丁基酯组和一个受植物保护的矿井,增强了其稳定性和在不同反应条件下的处理能力.溴烷基化合物侧链为进一步功能化提供了多功能性处理器,例如核生殖替代或交叉反应.其立体化学纯度(S-配置)确保了对不对称合成的精确控制.三丁基和博克保护组为选择性的脱保战略提供了便利,使其对多步骤合成路线具有价值.该化合物对于复杂的生物活性分子和聚胺术的制作特别有用.

英文名称(S)-Tert-Butyl 5-Bromo-2-((Tert-Butoxycarbonyl)Amino)Pentanoate
中文名称(S)-5-溴-2-((叔丁氧羰基)氨基)戊酸叔丁酯
IUPAC名称tert-butyl (S)-5-bromo-2-((tert-butoxycarbonyl)amino)pentanoate
其它别名5-溴-N-叔丁氧羰基-L-正缬氨酸叔丁酯; N-Boc-5-Bromo-L-Norvaline Tert-Butyl Ester
CAS编号91229-86-6
MFCD编号:MFCD22576481
EINECS号:859-186-4
分子式:C14H26BrNO4分子量:352.26
产品CID: 1947086
产品分类有机原料→分子砌块→手性化合物→手性砌块

相似结构搜索
InChIKey: UOJPSBYBSNFVHA-JTQLQIEISA-N
InChI=1S/C14H26BrNO4/c1-13(2,3)19-11(17)10(8-7-9-15)16-12(18)20-14(4,5)6/h10H,7-9H2,1-6H3,(H,16,18)/t10-/m0/s1
计算化学: 氢键受体数4.0氢键供体数1.0可旋转键数5.0

相似化合物

123004-74-0 90194-99-3 2356109-99-2

MSDS等安全信息

GHS符号GHS07
警示词Warning
危险描述H302-H315-H319-H335
防范说明P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

上下游产品

-5-hydroxypentanoatetert-butyl (S)-2-(tert-butyloxycarbonyl)amino-5-hydroxypentanoate N-tert-butoxycarbonyl glutamic acid tert-butyl ester tert-butyl dicarbonatedi-tert-butyl dicarbonate L-glutamic acid 1-tert-butyl ester 5-methyl ester N-B°C-L-proline tert-butyl ester 5-(N-Benzyloxy-acetimidoyloxy)-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester 5-(N-Benzyloxy-acetimidoyloxy)-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester α-(tert-butyloxycarbonyl)-N-acetyl-N-(benzyloxy)-L-ornithineα-tert-butyl Nα-(tert-butyloxycarbonyl)-N-acetyl-N-(benzyloxy)-L-ornithine

合成工艺路线路线简述

90194-99-3 = 91229-86-6
反应条件:1.1 Reagents: Carbon Tetrabromide,Triphenylphosphine Solvents: Dichloromethane; 0 °C; 20 Min,0 °C1.2 Reagents: Water Solvents: Hexane,Ethyl Acetate; 0 °C
标题:[13C3,15N1]-Labeled Isodesmosine: A Potential Internal Standard For Lc-Ms/ms Analysis Of Desmosines In Elastin Degradation
作者:Tanigawa,Takahiro; Et Al
参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2015 卷标:25(10) 页码:2046-2049]

24277-39-2 = 91229-86-6
反应条件:1.1 Reagents: 4-Methylmorpholine,Isobutyl Chloroformate Solvents: Tetrahydrofuran1.2 Reagents: Sodium Borohydride2.1 Reagents: Carbon Tetrabromide,Triphenylphosphine Solvents: Dichloromethane
标题:Facile New Method For Preparation Of Optically Active Protected Proline
作者:Yamaguchi,Jun-Ichi; Et Al
参考文献:Chemistry Letters 日期:1996 卷标:(8) 页码:621-622]

= 91229-86-6 [标题:Reaction Conditions
标题:Utility Of Tetrathiomolybdate And Tetraselenotungstate: Efficient Synthesis Of Cystine,Selenocystine,And Their Higher Homologs
作者:Bhat,Ramakrishna G.; Et Al
参考文献:Tetrahedron Letters 日期:2003 卷标:44(28) 页码:5251-5253]

= 91229-86-6 [标题:Reaction Conditions
标题:Synthesis Of Nα,Nδ-Protected Nδ-Hydroxy-L-Ornithine From L-Glutamic Acid
作者:Olsen,Richard K.; Et Al
参考文献:Journal Of Organic Chemistry 日期:1984 卷标:49(19) 页码:3527-34]

81477-94-3 = 91229-86-6
反应条件:1.1 Reagents: Potassium Hydroxide Catalysts: Cinchonanium,1-(9-Anthracenylmethyl)-9-(2-Propenyloxy)-,Bromide,(8α,9R)- Solvents: Toluene,Water; 14 H,Rt2.1 Reagents: Citric Acid Solvents: Tetrahydrofuran,Water; Overnight,Rt3.1 Reagents: Triethylamine Solvents: Dimethylformamide; Rt4.1 Reagents: Lithium Chloride,Sodium Borohydride Solvents: Ethanol,Tetrahydrofuran; 10 Min,Rt; Rt -> 0 °C4.2 Solvents: Ethanol,Tetrahydrofuran; 0 °C; Overnight,0 °C -> Rt5.1 Reagents: Triphenylphosphine,Bromine Solvents: Dichloromethane; Rt -> 0 °C; 0 °C; 20 Min,0 °C5.2 Reagents: Imidazole Solvents: Dichloromethane; 1 Min,0 °C; 2 H,0 °C
标题:Synthesis Of (ε-13C-,ε-15N)-Enriched L-Lysine - Establishing Schemes For The Preparation Of All Possible 13C And 15N Isotopomers Of L-Lysine,L-Ornithine,And L-Proline
作者:Siebum,Arjan H. G.; Et Al
参考文献:European Journal Of Organic Chemistry 日期:2004 卷标:(21) 页码:4391-4396]

90194-99-3 = 91229-86-6
反应条件:1.1 Reagents: Carbon Tetrabromide,Triphenylphosphine Solvents: Dichloromethane
标题:Facile New Method For Preparation Of Optically Active Protected Proline
作者:Yamaguchi,Jun-Ichi; Et Al
参考文献:Chemistry Letters 日期:1996 卷标:(8) 页码:621-622]

24277-38-1 = 91229-86-6
反应条件:1.1 Reagents: Lithium Chloride,Sodium Borohydride Solvents: Ethanol,Tetrahydrofuran; 10 Min,Rt; Rt -> -5 °C1.2 Solvents: Ethanol,Tetrahydrofuran; -5 °C; 17 H,-5 °C2.1 Reagents: Carbon Tetrabromide,Triphenylphosphine Solvents: Dichloromethane; 0 °C; 20 Min,0 °C2.2 Reagents: Water Solvents: Hexane,Ethyl Acetate; 0 °C
标题:[13C3,15N1]-Labeled Isodesmosine: A Potential Internal Standard For Lc-Ms/ms Analysis Of Desmosines In Elastin Degradation
作者:Tanigawa,Takahiro; Et Al
参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2015 卷标:25(10) 页码:2046-2049]

24277-38-1 = 91229-86-6
反应条件:1.1 Reagents: Lithium Chloride,Sodium Borohydride Solvents: Ethanol,Tetrahydrofuran; 10 Min,Rt; Rt -> 0 °C1.2 Solvents: Ethanol,Tetrahydrofuran; 0 °C; Overnight,0 °C -> Rt2.1 Reagents: Triphenylphosphine,Bromine Solvents: Dichloromethane; Rt -> 0 °C; 0 °C; 20 Min,0 °C2.2 Reagents: Imidazole Solvents: Dichloromethane; 1 Min,0 °C; 2 H,0 °C
标题:Synthesis Of (ε-13C-,ε-15N)-Enriched L-Lysine - Establishing Schemes For The Preparation Of All Possible 13C And 15N Isotopomers Of L-Lysine,L-Ornithine,And L-Proline
作者:Siebum,Arjan H. G.; Et Al
参考文献:European Journal Of Organic Chemistry 日期:2004 卷标:(21) 页码:4391-4396]

24424-99-5 + 79640-72-5 = 91229-86-6
反应条件:1.1 Reagents: Triethylamine Solvents: Dimethylformamide; Rt2.1 Reagents: Lithium Chloride,Sodium Borohydride Solvents: Ethanol,Tetrahydrofuran; 10 Min,Rt; Rt -> 0 °C2.2 Solvents: Ethanol,Tetrahydrofuran; 0 °C; Overnight,0 °C -> Rt3.1 Reagents: Triphenylphosphine,Bromine Solvents: Dichloromethane; Rt -> 0 °C; 0 °C; 20 Min,0 °C3.2 Reagents: Imidazole Solvents: Dichloromethane; 1 Min,0 °C; 2 H,0 °C
标题:Synthesis Of (ε-13C-,ε-15N)-Enriched L-Lysine - Establishing Schemes For The Preparation Of All Possible 13C And 15N Isotopomers Of L-Lysine,L-Ornithine,And L-Proline
作者:Siebum,Arjan H. G.; Et Al
参考文献:European Journal Of Organic Chemistry 日期:2004 卷标:(21) 页码:4391-4396]

212121-62-5 = 91229-86-6
反应条件:1.1 Reagents: Citric Acid Solvents: Tetrahydrofuran,Water; Overnight,Rt2.1 Reagents: Triethylamine Solvents: Dimethylformamide; Rt3.1 Reagents: Lithium Chloride,Sodium Borohydride Solvents: Ethanol,Tetrahydrofuran; 10 Min,Rt; Rt -> 0 °C3.2 Solvents: Ethanol,Tetrahydrofuran; 0 °C; Overnight,0 °C -> Rt4.1 Reagents: Triphenylphosphine,Bromine Solvents: Dichloromethane; Rt -> 0 °C; 0 °C; 20 Min,0 °C4.2 Reagents: Imidazole Solvents: Dichloromethane; 1 Min,0 °C; 2 H,0 °C
标题:Synthesis Of (ε-13C-,ε-15N)-Enriched L-Lysine - Establishing Schemes For The Preparation Of All Possible 13C And 15N Isotopomers Of L-Lysine,L-Ornithine,And L-Proline
作者:Siebum,Arjan H. G.; Et Al
参考文献:European Journal Of Organic Chemistry 日期:2004 卷标:(21) 页码:4391-4396

📜Tert-Butyl (S)-2-((Tert-Butoxycarbonyl)Amino)-5-Hydroxypentanoate置于咪唑,溴,三苯基膦体系中,用二氯甲烷作为反应溶剂,化学反应 2.0H,以81%的收率获得产物5-溴-N-叔丁氧羰基-L-正缬氨酸叔丁酯
参考文献:(-13C-,-15N)-富集l-赖氨酸的合成建立所有可能的 L-赖氨酸,L-鸟氨酸和 L-脯氨酸的 13C 和 15N 同位素异构体的制备方案
标题:(-13C-,-15N)-富集l-赖氨酸的合成建立所有可能的 L-赖氨酸,L-鸟氨酸和 L-脯氨酸的 13C 和 15N 同位素异构体的制备方案
摘要:在本文中,我们描述了一种简单的合成策略,通过正确的合理适应,可以直接获得 L-谷氨酸,L-鸟氨酸,L-脯氨酸,L-赖氨酸和 L-α 氨基己二酸的任何 13C/15N 同位素异构体. 该策略还允许以高产量和光学纯度获得非蛋白质氨基酸,如 L-瓜氨酸.(© Wiley-Vch Verlag Gmbh & Co. Kgaa,69451 Weinheim,Germany,2004)
DOI:10.1002/ejoc.200400370