(E)-(S)-4-tert-Butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enoic acid methyl ester | 134419-08-2

• 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: (E)-(S)-4-tert-Butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enoic acid methyl ester
• 英文别名: methyl (E,4S)-5-[tert-butyl(dimethyl)silyl]oxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]pent-2-enoate
• CAS: 134419-08-2
• 化学式: C₁₇H₃₃NO₅Si
• 分子量: 359.538
• InChiKey: UNKIIWVFCLKRIZ-NHAQELONSA-N

物化性质

• 沸点：
  415.3±45.0 °C(Predicted)
• 密度：
  0.995±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-(S)-4-tert-Butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enoic acid methyl ester 在 lithium hydroxide monohydrate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 methyl (S,E)-N-(4-((tert-butoxycarbonyl)amino)-5-((tert-butyldimethylsilyl)oxy)pent-2-enoyl)-N-methylglycinate
  参考文献：
  名称：

  环二肽BE-43547A2：胰腺癌干细胞的合成及活性

  摘要：

  一批15线性步骤以350 mg的规模完成了环状二肽BE-43547A 2的不对称全合成。合成的特征是通过α-羟基化以高达86：1的dr高度高度非对映选择性地构建α-羟基-β-酮酰胺。BE‐43547A 2显着降低了Panc-1细胞培养物中胰腺癌干细胞（PCSC）的百分比，并显着降低了Panc-1细胞在肿瘤球形成中的能力。体内肿瘤起始试验是癌症干细胞试验的金标准，证实了BE-43547A 2可以消除Panc-1细胞的肿瘤发生。BE‐43547A 2的抗PCSC活性 可以使这种depsipeptide支架成为发现新的靶向PCSC的药物的有希望的起点。

  DOI：

  10.1002/anie.201709744
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (E)-(S)-4-tert-Butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enoic acid methyl ester
  参考文献：
  名称：

  环二肽BE-43547A2：胰腺癌干细胞的合成及活性

  摘要：

  一批15线性步骤以350 mg的规模完成了环状二肽BE-43547A 2的不对称全合成。合成的特征是通过α-羟基化以高达86：1的dr高度高度非对映选择性地构建α-羟基-β-酮酰胺。BE‐43547A 2显着降低了Panc-1细胞培养物中胰腺癌干细胞（PCSC）的百分比，并显着降低了Panc-1细胞在肿瘤球形成中的能力。体内肿瘤起始试验是癌症干细胞试验的金标准，证实了BE-43547A 2可以消除Panc-1细胞的肿瘤发生。BE‐43547A 2的抗PCSC活性 可以使这种depsipeptide支架成为发现新的靶向PCSC的药物的有希望的起点。

  DOI：

  10.1002/anie.201709744

文献信息

• Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines. Conformationally constrained L-glutamate analogs
  作者：Keiko Shimamoto、Michiko Ishida、Haruhikio Shinozaki、Yasufumi Ohfune

  DOI：10.1021/jo00013a018

  日期：1991.6

  To determine what conformations of L-glutamate (L-Glu) activate that compound's different receptors in the mammalian central nervous system, four diastereomeric L-2-(carboxycyclopropyl)glycines, 1-4, which are conformationally constrained analogues of the extended and folded conformers of L-Glu, were synthesized and subjected to neutrophysiological assay. Compounds 1-4 were efficiently synthesized from chiral amino acids. Cyclopropanation of the (2S)-2-amino-3-butenol derivative 5b gave intermediates for the synthesis of all four diastereomers. Stereoselective cyclopropanation of both the alpha,beta-unsaturated gamma-lactam 16 and the delta-lactone 19 gave precursors of (2S,1'S,2'R)-3 and (2S,1'R,2'S)-4, respectively. Neurophysiological assays of 1-4 performed with the newborn rat spinal cord demonstrated that the compounds induced a variety of depolarizing effects. The results of the assays strongly suggested that the N-methyl-D-aspartic acid (NMDA) receptor is activated by the folded conformer of L-Glu and that the extended conformer of L-Glu activates the metabotropic L-Glu receptor. The four analogous D-2-(carboxycyclopropyl)glycines (D-1-D-4), which were synthesized from (2R)-5b, proved to be NMDA agonists.
• Efficient and stereoselective synthesis of (2S,3S,4S)-3,4-dihydroxyglutamic acid via intramolecular epoxidation
  作者：Hyeonjeong Kim、Dongwon Yoo、Soo Young Choi、Young Keun Chung、Young Gyu Kim

  DOI：10.1016/j.tetasy.2008.07.036

  日期：2008.8

  The stereoselective synthesis of bioactive (2S,3S,4S)-3,4-dihydroxyglutamic acid hydrochloride salt was achieved. The key step involved an intramolecular nucleophilic epoxidation of homochiral gamma-amino- alpha,beta-unsaturated ester 5 containing an N-hydroperoxymethyl group followed by regioselective opening of the resulting epoxide with neighboring group participation of the N-Boc group. The diastereoselectivity was more than 20:1 by H-1 NMR spectroscopy. Thus, (2S,3S,4S)-3,4-dihydroxyglutamic acid hydrochloride salt was prepared from configurationally stable N-BOC-D-Serinal 4 in 25% overall yield over nine steps. (C) 2008 Elsevier Ltd. All rights reserved.
• Gonda Josef, Helland Anne-Charlotte, Ernst Beat, Bellu Daniel, Synthesis, (1993) N 7, S 729-733
  作者：Gonda Josef, Helland Anne-Charlotte, Ernst Beat, Bellu Daniel

  DOI：——

  日期：——