CAS: 828254-16-6; (R)-3-((((9H-Fluoren-9-yl)Methoxy)Carbonyl)Amino)-2-Benzylpropanoic Acid

英文名称(R)-3-((((9H-Fluoren-9-yl)Methoxy)Carbonyl)Amino)-2-Benzylpropanoic Acid
中文名称(R)-3-((((9H-芴-9-基)甲氧基)羰基)氨基)-2-苄基丙酸
IUPAC名称(R)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-benzylpropanoic acid
其它别名Fmoc-(R)-2-苄基-3-N-叔丁氧羰基氨基丙酸; Fmoc-(R)-3-Amino-2-Benzylpropanoic Acid
CAS编号828254-16-6
MFCD编号:MFCD07372498
分子式:C25H23NO4分子量:401.46
产品CID: 1818306
产品分类有机原料→分子砌块→芳环类化合物→苯类化合物

相似结构搜索
InChIKey: NZMKXKRMTSBQFS-GOSISDBHSA-N
InChI=1S/C25H23NO4/c27-24(28)18(14-17-8-2-1-3-9-17)15-26-25(29)30-16-23-21-12-6-4-10-19(21)20-11-5-7-13-22(20)23/h1-13,18,23H,14-16H2,(H,26,29)(H,27,28)/t18-/m1/s1
计算化学: 氢键受体数3.0氢键供体数2.0可旋转键数7.0

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

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (R)-α-benzyl-β-aminopropanoic acid 2-Benzylacrylic acid ethyl ester benzyl bromide

合成工艺路线路线简述

5669-19-2 = 828254-16-6
反应条件:1.1 Reagents: Diisopropylcarbodiimide Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; 10 Min,0 °C; 0 °C -> Rt; 16 H,Rt2.1 Solvents: Tetrahydrofuran; Rt -> 72 °C; 24 H,72 °C; 72 °C -> Rt3.1 Reagents: Lithium Hydroxide,Hydrogen Peroxide Solvents: Tetrahydrofuran,Water; 45 Min,0 °C3.2 Reagents: Sodium Sulfite Solvents: Water; 30 Min,0 °C -> Rt4.1 Reagents: Hydrogen,Ammonia Catalysts: Palladium Solvents: Methanol,Water; 72 H,Rt4.2 Reagents: Sodium Bicarbonate Solvents: Tetrahydrofuran,Water; Rt -> 0 °C; 2 H,0 °C -> Rt
标题:Preparation Of Perfluoroalkane-Tagged Chiral Auxiliaries And Their Application To Stereoselective Synthesis Of A β2-Amino Acid Building Block
作者:Vogtle,Markus M.; Et Al
参考文献:Arkivoc (Gainesville 日期:2008 卷标:(15) 页码:210-224]

82911-69-1 = 828254-16-6
反应条件:1.1 Reagents: Hydrogen,Ammonia Catalysts: Palladium Solvents: Methanol,Water; 72 H,Rt1.2 Reagents: Sodium Bicarbonate Solvents: Tetrahydrofuran,Water; Rt -> 0 °C; 2 H,0 °C -> Rt
标题:Preparation Of Perfluoroalkane-Tagged Chiral Auxiliaries And Their Application To Stereoselective Synthesis Of A β2-Amino Acid Building Block
作者:Vogtle,Markus M.; Et Al
参考文献:Arkivoc (Gainesville 日期:2008 卷标:(15) 页码:210-224]

= 828254-16-6
反应条件:1.1 Reagents: Lithium Hydroxide,Hydrogen Peroxide Solvents: Tetrahydrofuran,Water; 45 Min,0 °C1.2 Reagents: Sodium Sulfite Solvents: Water; 30 Min,0 °C -> Rt2.1 Reagents: Hydrogen,Ammonia Catalysts: Palladium Solvents: Methanol,Water; 72 H,Rt2.2 Reagents: Sodium Bicarbonate Solvents: Tetrahydrofuran,Water; Rt -> 0 °C; 2 H,0 °C -> Rt
标题:Preparation Of Perfluoroalkane-Tagged Chiral Auxiliaries And Their Application To Stereoselective Synthesis Of A β2-Amino Acid Building Block
作者:Vogtle,Markus M.; Et Al
参考文献:Arkivoc (Gainesville 日期:2008 卷标:(15) 页码:210-224]

622-33-3 = 828254-16-6
反应条件:1.1 Solvents: Tetrahydrofuran; Rt -> 72 °C; 24 H,72 °C; 72 °C -> Rt2.1 Reagents: Lithium Hydroxide,Hydrogen Peroxide Solvents: Tetrahydrofuran,Water; 45 Min,0 °C2.2 Reagents: Sodium Sulfite Solvents: Water; 30 Min,0 °C -> Rt3.1 Reagents: Hydrogen,Ammonia Catalysts: Palladium Solvents: Methanol,Water; 72 H,Rt3.2 Reagents: Sodium Bicarbonate Solvents: Tetrahydrofuran,Water; Rt -> 0 °C; 2 H,0 °C -> Rt
标题:Preparation Of Perfluoroalkane-Tagged Chiral Auxiliaries And Their Application To Stereoselective Synthesis Of A β2-Amino Acid Building Block
作者:Vogtle,Markus M.; Et Al
参考文献:Arkivoc (Gainesville 日期:2008 卷标:(15) 页码:210-224]

106391-85-9 + 195324-87-9 = 828254-16-6
反应条件:1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran,Hexane; 20 Min,-78 °C1.2 Solvents: Tetrahydrofuran; -78 °C; 6 H,-78 °C; 16 H,-78 °C -> Rt1.3 Reagents: Ammonium Chloride Solvents: Water2.1 Reagents: Diisopropylcarbodiimide Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; 10 Min,0 °C; 0 °C -> Rt; 16 H,Rt3.1 Solvents: Tetrahydrofuran; Rt -> 72 °C; 24 H,72 °C; 72 °C -> Rt4.1 Reagents: Lithium Hydroxide,Hydrogen Peroxide Solvents: Tetrahydrofuran,Water; 45 Min,0 °C4.2 Reagents: Sodium Sulfite Solvents: Water; 30 Min,0 °C -> Rt5.1 Reagents: Hydrogen,Ammonia Catalysts: Palladium Solvents: Methanol,Water; 72 H,Rt5.2 Reagents: Sodium Bicarbonate Solvents: Tetrahydrofuran,Water; Rt -> 0 °C; 2 H,0 °C -> Rt
标题:Preparation Of Perfluoroalkane-Tagged Chiral Auxiliaries And Their Application To Stereoselective Synthesis Of A β2-Amino Acid Building Block
作者:Vogtle,Markus M.; Et Al
参考文献:Arkivoc (Gainesville 日期:2008 卷标:(15) 页码:210-224

📜2-苄基乙酰乙酸乙酯置于10Percent Pd/c 甲酸铵,碳酸氢钠,三乙胺,Lithium Hexamethyldisilazane体系中,用四氢呋喃,甲醇,水,N,N-二甲基甲酰胺作为反应溶剂,化学反应 30.5H,反应生成 Fmoc-(R)-2-苄基-3-N-叔丁氧羰基氨基丙酸
参考文献:通过手性异恶唑烷酮有效合成对映体纯的β2-氨基酸.
标题:通过手性异恶唑烷酮有效合成对映体纯的β2-氨基酸.
摘要:我们报告了一种实用且可扩展的合成路线,用于制备α-取代的β-氨基酸(β(2)-氨基酸).将衍生自α-甲基苄基胺的手性羟胺迈克尔加成至α-烷基丙烯酸酯,然后环化,得到α-取代的异恶唑烷酮的非对映异构体混合物.这些非对映异构体可通过柱色谱法分离.纯化的异恶唑烷酮的随后氢化,然后进行fmoc保护,得到对映体纯的fmoc-β(2)-氨基酸,可用于合成β-肽.该途径提供了获得保护的β(2)-氨基酸的两种对映异构体的途径.
DOI:10.1021/jo026738B