(2S)-N-(3,3,3-trifluoro-2-methoxy-1-oxo-2-phenylpropoxy)-L-valine methyl ester | 70363-24-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-N-(3,3,3-trifluoro-2-methoxy-1-oxo-2-phenylpropoxy)-L-valine methyl ester
• 英文别名: N-(S)-MTPA-L-valine methyl ester；methyl (2S)-3-methyl-2-[[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]amino]butanoate
• CAS: 70363-24-5
• 化学式: C₁₆H₂₀F₃NO₄
• 分子量: 347.334
• InChiKey: SCKUQXHKTIKRLE-WFASDCNBSA-N

物化性质

• 沸点：
  409.8±45.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (3-(3-(((S)-1-carboxy-2-methylpropyl)carbamoyl)-9H-pyrido[3,4-b]indole-1-yl)propanoyl)-L-proline 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 水 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.17h， 生成 (2S)-N-(3,3,3-trifluoro-2-methoxy-1-oxo-2-phenylpropoxy)-L-valine methyl ester
  参考文献：
  名称：

  HR-MALDI-MS Imaging Assisted Screening of β-Carboline Alkaloids Discovered from Mycena metata

  摘要：

  Fruiting bodies of Mycena metata were screened for the presence of new secondary metabolites by means of HPLC-UV, LC-HR-ESIMS, and high-resolution matrix-assisted laser desorption/ionization mass spectrometry imaging (HR-MALDI-MS imaging). Thus, a new beta-carboline alkaloid, 6-hydroxymetatacarboline D (1d), was isolated from fruiting bodies of M. metata. 6-Hydroxymetatacarboline D consists of a highly substituted beta-carboline skeleton, which is likely to be derived biosynthetically from L-tryptophan, 2-oxoglutaric acid, L-threonine, and L-proline. The structure of the alkaloid was established by 2D NMR spectroscopic methods and HR-ESIMS. Moreover, by extensive application of LC-HR-ESIMS, LC-HR-ESIMS/MS, and LC-HR-ESIMS3 techniques we were able to elucidate the structures of a number of accompanying beta-carboline alkaloids, 1a-1c, 1e-1i, and 2a-2g, structurally closely related to 6-hydroxymetatacarboline D, which are present in M. metata in minor amounts. The absolute configuration of the stereogenic centers of the beta-carboline alkaloids was determined by GC-MS comparison with authentic synthetic samples after hydrolytic cleavage and derivatization of the resulting amino acids.

  DOI：

  10.1021/np300455a

文献信息

• Asymmetric Synthesis of α-Amino Acids Based on Carbon Radical Addition to Glyoxylic Oxime Ether
  作者：Hideto Miyabe、Chikage Ushiro、Masafumi Ueda、Kumiko Yamakawa、Takeaki Naito

  DOI：10.1021/jo991353n

  日期：2000.1.1

  the sultam auxiliary by standard hydrolysis, afforded the enantiomerically pure D-valine (R)-12 without any loss of stereochemical purity. To evaluate the new methodology, a variety of alkyl radicals were employed in the addition reaction which gave the alkylated products 7 with excellent diastereoselectivity, allowing access to a wide range of enantiomerically pure natural and unnatural alpha-amino

  报道了基于非对映选择性碳自由基加成乙醛酸亚胺衍生物的α-氨基酸的首次不对称合成。在25°C下，由i-PrI，Bu（3）SnH和Et（3）B在CH（2）Cl（2）中生成的异丙基向非手性乙醛酸肟醚1的区域选择性地在亚氨基上进行。肟醚基的碳原子可得到极佳的C-异丙基化产物2收率。乙醛肟肟1和醛肟醚4的竞争反应表明，乙醛肟肟醚对亲核碳自由基的反应性增强了相邻的吸电子取代基的结构。因此，与未活化的醛肟醚4相反，即使在-78℃下，向乙醛氧基肟醚1的烷基加成也顺利进行。通过使用Oppolzer的樟脑素作为手性助剂，可以实现对乙醛酸肟醚碳自由基加成的高度立体控制。樟脑素衍生物6与异丙基的甲炔基自由基介导的反应在-78℃下得到C-异丙基化产物的96：4非对映异构体混合物7a。通过用Mo（CO）（6）处理还原去除主要的非对映异构体（R）-7a的苄氧基，然后通过标准水解去除sultam助剂，得到对映体纯的D-缬氨酸（R）-
• Expeditious synthesis of mosher amides using a solid supported carbodiimide
  作者：Maciej Adamczyk、Jeffrey R. Fishpaugh

  DOI：10.1016/0040-4039(96)01617-6

  日期：1996.9

  A novel method of Mosher amide synthesis using a solid supported carbodiimide in CDCl3 is described. Estimation of optical purity can be promptly achieved by direct NMR analysis of the reaction solvent.

  描述了使用在CDCl 3中的固体负载的碳二亚胺合成Mosher酰胺的新方法。光学纯度的估计可以通过反应溶剂的直接NMR分析迅速完成。
• Elucidation of the absolute configurations of amino acids and amines by the modified mosher's method
  作者：Takenori Kusumi、Toshiro Fukushima、Ikuko Ohtani、Hiroshi Kakisawa

  DOI：10.1016/0040-4039(91)80655-p

  日期：1991.6

  Application of the modified Mosher's method to the N-MTPA derivatives of several amino acid esters and acyclic amines indicates that this method may be generally used to determine the absolute configurations of the alpha-carbons of amino compounds of less than 0.1 mg amount.
• HR-MALDI-MS Imaging Assisted Screening of β-Carboline Alkaloids Discovered from <i>Mycena metata</i>
  作者：Robert J. R. Jaeger、Marc Lamshöft、Sebastian Gottfried、Michael Spiteller、Peter Spiteller

  DOI：10.1021/np300455a

  日期：2013.2.22

  Fruiting bodies of Mycena metata were screened for the presence of new secondary metabolites by means of HPLC-UV, LC-HR-ESIMS, and high-resolution matrix-assisted laser desorption/ionization mass spectrometry imaging (HR-MALDI-MS imaging). Thus, a new beta-carboline alkaloid, 6-hydroxymetatacarboline D (1d), was isolated from fruiting bodies of M. metata. 6-Hydroxymetatacarboline D consists of a highly substituted beta-carboline skeleton, which is likely to be derived biosynthetically from L-tryptophan, 2-oxoglutaric acid, L-threonine, and L-proline. The structure of the alkaloid was established by 2D NMR spectroscopic methods and HR-ESIMS. Moreover, by extensive application of LC-HR-ESIMS, LC-HR-ESIMS/MS, and LC-HR-ESIMS3 techniques we were able to elucidate the structures of a number of accompanying beta-carboline alkaloids, 1a-1c, 1e-1i, and 2a-2g, structurally closely related to 6-hydroxymetatacarboline D, which are present in M. metata in minor amounts. The absolute configuration of the stereogenic centers of the beta-carboline alkaloids was determined by GC-MS comparison with authentic synthetic samples after hydrolytic cleavage and derivatization of the resulting amino acids.