methyl (2S)-5-diazo-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate | 88668-76-2

• 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: methyl (2S)-5-diazo-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate
• 英文别名: methyl 5-diazo-4-oxo-N-trifluoroacetyl-(2S)-norvalinate；(S)-N-trifluoroacetyl-5-diazo-4-oxonorvaline methyl ester；methyl (2S)-5-diazo-4-oxo-2-trifluoroacetamidopentanoate；(S)-5-diazo-4-oxo-2-(2,2,2-trifluoro-acetylamino)-valeric acid methyl ester；(S)-5-Diazo-4-oxo-2-(2,2,2-trifluor-acetylamino)-valeriansaeure-methylester；methyl (2S)-5-diazo-4-oxo-2-[(2,2,2-trifluoroacetyl)amino]pentanoate
• CAS: 88668-76-2
• 化学式: C₈H₈F₃N₃O₄
• 分子量: 267.164
• InChiKey: PPSDAYOPRRCDBO-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (2S)-5-diazo-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate 在 氢溴酸 、 溶剂黄146 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 24.0h， 生成 (S)-N-trifluoroacetyl-3-(2-aminothiazol-4-yl)alanine methyl ester
  参考文献：
  名称：

  氮杂色氨酸衍生物的合成

  摘要：

  天冬氨酸（的光学活性和外消旋异构体1）转化成相应的Ñ -三氟乙酰基-5-溴-4- oxonorvaline甲酯（6，R = Me）的和ñ -三氟乙酰基-3-甲酰基丙氨酸甲酯13，这是在合成β-杂芳基取代的α-氨基酸中用作起始化合物。

  DOI：

  10.1002/jhet.5570310524
• 作为产物：
  描述：

  (S)-(-)-2-(三氟乙酰胺)琥珀酸酐 在 氯化亚砜 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.83h， 生成 methyl (2S)-5-diazo-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate
  参考文献：
  名称：

  Gani, David; Young, Douglas W., Journal of the Chemical Society. Perkin transactions I, 1983, # 10, p. 2393 - 2398

  摘要：

  DOI：

文献信息

• Synthesis of (2S,3S)-[3-2H1]- and (2S,3R)-[2,3-2H2]-proline
  作者：Petra Dieterich、Douglas W. Young

  DOI：10.1016/s0040-4039(00)73933-5

  日期：1993.1

  of a ketene intermediate has led to an effective synthesis of samples of the amino acid proline which are stereospecifically labelled on the β-carbon. Since samples of stereospecifically labelled pyroglutamic acid derivatives are prepared in the route, other stereospecifically labelled, biologically important amino acids may be accessed by the synthesis.

  分子内捕获乙烯酮中间体的条件的发现已导致有效合成的氨基酸脯氨酸样品，这些样品在β-碳上进行了立体定向标记。由于在该途径中制备了立体特异性标记的焦谷氨酸衍生物的样品，因此合成中可能会获得其他立体特异性标记的，生物学上重要的氨基酸。
• Two separate and distinct syntheses of stereospecifically deuteriated samples of (2S)-proline
  作者：Paul Barraclough、Petra Dieterich、Caroline A. Spray、Douglas W. Young

  DOI：10.1039/b601097k

  日期：——

  were then converted into (2S,3S)-[3-(2)H1]- and (2S,3R)-[2,3-(2)H2]-proline, 1a and 1b respectively. The second synthesis provides (2S)-[3,3-(2)H2]-, (2S,3S)- and (2S,3R)-[3-(2)H1]-proline, 1d, 1a and 1c respectively, and has as its key step the highly stereoselective hydrolysis of the silylenol ethers 14 and 14a respectively in which deuteriation or protonation occurs from the re-face of the enol ether

  报道了在β-碳原子上立体定向氘化的氨基酸L-脯氨酸样品的两种不同的合成。在这些方法中的第一方法中，通过化学-酶促合成制备的标记的重氮酮6已经在碱性条件下被光解，以通过水解和分子内捕集所得的烯酮中间体9而得到相应的标记的焦谷氨酸甲酯10。然后将它们转化为（2S，3S）-[3-（2）H1]-和（2S，3R）-[2，3-（2）H2]-脯氨酸，分别为1a和1b。第二种合成分别提供（2S）-[3,3-（2）H2]-，（2S，3S）-和（2S，3R）-[3-（2）H1]-脯氨酸，1d，1a和1c ，并且是关键步骤的甲硅烷基醚14和14a的高度立体选择性水解，其中从烯醇醚的表面发生氘化或质子化。
• Synthesis of an external β-turn based on the GLDV motif of cell adhesion proteins
  作者：David E. Davies、Paul M. Doyle、R.Duncan Farrant、Richard D. Hill、Peter B. Hitchcock、Paul N. Sanderson、Douglas W. Young

  DOI：10.1016/j.tetlet.2003.09.170

  日期：2003.12

  The (3S,6S,10S)-7/5 bicyclic lactam 4, designed as an external turn constraint, was synthesised by a new stereoselective route involving Eschenmoser condensation. Calculated preferred conformations compare well with the preferred solid state conformation. obtained by X-ray crystallography. The lactam 4 was not a turn mimic in its own right but Could be used as an external constraint to prepare the cyclic peptide 29 containing the integrin recognition motif GLDV. High-resolution NMR measurements were consistent with this compound having a single backbone conformation. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of an external beta-turn based on the GLDV motif of cell adhesion proteins
  作者：David E. Davies、Paul M. Doyle、Richard D. Hill、Douglas W. Young

  DOI：10.1016/j.tet.2004.09.037

  日期：2005.1

  The (3S,6S, 10S)-7/5 bicyclic lactam 8, designed as an external turn constraint, was synthesised by a new stereoselective route involving Eschenmoser condensation. The cyclic peptide 35 containing the integrin recognition motif GLDV added across the amino and carboxyl groups of the lactam external constraint 8 was prepared. (C) 2004 Elsevier Ltd. All rights reserved.
• Liwschitz et al., Journal of the Chemical Society, 1959, p. 1308
  作者：Liwschitz et al.

  DOI：——

  日期：——