methyl (3R)-3-[(tert-butoxycarbonyl)amino]-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate | 146877-30-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (3R)-3-[(tert-butoxycarbonyl)amino]-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate
• 英文别名: methyl (3R)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 146877-30-7
• 化学式: C₁₄H₂₅NO₆
• 分子量: 303.356
• InChiKey: UEBNGWQTLYIKDK-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (3R)-3-[(tert-butoxycarbonyl)amino]-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate 在 palladium on activated charcoal 正丁基锂 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 15.5h， 生成
  参考文献：
  名称：

  9(R)-N-BOC-Ahda 甲酯的立体控制全合成

  摘要：

  描述了以光学纯形式首次全合成 9(R)-N-BOC-Ahda 甲酯的有效收敛路线。

  DOI：

  10.1246/cl.1992.2385
• 作为产物：
  描述：

  methyl (3R,4S)-3-butylamino-4,5-(isopropylidenedioxy)pentanoate 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 methyl (3R)-3-[(tert-butoxycarbonyl)amino]-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate
  参考文献：
  名称：

  9(R)-N-BOC-Ahda 甲酯的立体控制全合成

  摘要：

  描述了以光学纯形式首次全合成 9(R)-N-BOC-Ahda 甲酯的有效收敛路线。

  DOI：

  10.1246/cl.1992.2385

文献信息

• Reactivity of Chiral α-Amidoalkylphenyl Sulfones with Stabilized Carbanions. Stereoselective Synthesis of Optically Active 1-Aminopyrrolizidine
  作者：Nicola Giri、Marino Petrini、Roberto Profeta

  DOI：10.1021/jo048882y

  日期：2004.10.1

  functionalized allylzinc reagents react with optically active α-amidoalkylphenyl sulfones to give N-carbamoylamino derivatives with variable levels of anti diastereoselectivity. Zinc enolates provide comparable results with respect to lithium enolates in terms of diastereoselectivity but afford β-amino ester derivatives in lower yield. The synthetic utility of the obtained chiral N-carbamoylamino esters is demonstrated

  金属烯醇化物和官能化试剂allylzinc与光学活性的反应α-amidoalkylphenyl砜，得到Ñ -carbamoylamino具有可变水平的衍生物反非对映选择性。就非对映选择性而言，烯醇锌提供与烯醇锂可比较的结果，但以较低的产率提供β-氨基酯衍生物。所获得的手性N-氨基甲酰基氨基酯的合成效用通过（-）-1-氨基吡咯烷核苷（用于制备各种生物活性物质的中心中间体）的第一对映选择性合成来证明。
• Synthesis of β-amino arylketones through the addition of ArLi derivatives to β-aminoesters
  作者：Paulo G Lima、Lucia C Sequeira、Paulo R.R Costa

  DOI：10.1016/s0040-4039(01)00358-6

  日期：2001.5

  2-Lithiumthiophene and 2-lithiumpyridine were allowed to react with iv-substituted beta -aminoesters. Only beta -amino arylketones were obtained from N-BOC, IV-H derivatives, while arylenoates were formed (retro-conjugate addition) from those substrates bearing N-Bn, N-H substituents, despite the aryllithium used. When the nitrogen is disubstituted (BOC and Bn), the product distribution depended on the nucleophile, leading to tertiary alcohols for 2-lithiumthiophene or ketones for 2-lithiumpyridine. Tertiary alcohols were also formed when PhLi was used as a nucleophile. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Stereoselective synthesis and preliminary evaluation of new d-3-heteroarylcarbonylalanines as ligands of the NMDA receptor
  作者：Paulo G. Lima、Rodrigo R.B. Caruso、Simone O. Alves、Renata F. Pessôa、Dayde L. Mendonça-Silva、Ricardo J. Nunes、François Noël、Newton G. Castro、Paulo R.R. Costa

  DOI：10.1016/j.bmcl.2004.06.062

  日期：2004.9

  New N-heteroarylcarbonylalanines of the D-series were stereoselectively prepared from enoates derived from D-mannitol. These compounds were active in binding and functional assays of the NMDA sub-type of glutamate receptors. A pyridine derivative inhibited MK801 binding, protected neurons from excitotoxic damage and blocked NMDA-induced currents in neurons. A thiophene derivative positively modulated the NMDA receptor, possibly through the allosteric glycine site. (C) 2004 Elsevier Ltd. All rights reserved.