(Z)-2-Benzyloxy-1-methoxy-1-(tert-butyldimethylsiloxy)ethene | 178872-58-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-2-Benzyloxy-1-methoxy-1-(tert-butyldimethylsiloxy)ethene
• 英文别名: (Z)-2-benzyloxy-1-methoxy-1-(tert-butyldimethylsilyloxy)ethene；tert-butyl-[(Z)-1-methoxy-2-phenylmethoxyethenoxy]-dimethylsilane
• CAS: 178872-58-7
• 化学式: C₁₆H₂₆O₃Si
• 分子量: 294.466
• InChiKey: LTQQXISKBUDMOV-SQFISAMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  20
• 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：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2-Benzyloxy-1-methoxy-1-(tert-butyldimethylsiloxy)ethene 、 (3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanal 在 magnesium bromide 作用下， 以 甲苯 为溶剂， 生成 Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate
  参考文献：
  名称：

  紫杉醇合成的新方法。立体选择性羟醛反应合成光学活性 3,7-dibenzyloxy-4,8-​​di-t-butyl-dimethylsiloxy-5,5-dimethyl-6-p-methoxybenzyloxy-2-octanone

  摘要：

  光学活性 3,7-dibenzyloxy-4,8-​​di-t-butyldimethylsiloxy-5,5-dimethyl-6-p-methoxybenzyloxy-2-octanone (2) 已通过 4-benzyloxy- 之间的非对映选择性羟醛反应合成5-叔丁基二甲基甲硅烷氧基-2,2-二甲基-3-对甲氧基-苄氧基戊醛(3)和乙烯酮甲硅烷基缩醛4，以MgBr2·OEt2为催化剂。手性戊醛 3 是通过使用手性路易斯酸的前手性醛 5 和烯酮甲硅烷基缩醛 4 的不对称羟醛反应合成的，或者通过衍生自 L-丝氨酸的手性醛 6 和衍生自异丁酸甲酯的烯醇锂之间的非对映选择性羟醛反应合成的。

  DOI：

  10.1246/cl.1995.179
• 作为产物：
  描述：

  2-苯基甲氧基乙酸甲酯 、 叔丁基二甲硅基三氟甲磺酸酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以70%的产率得到(Z)-2-Benzyloxy-1-methoxy-1-(tert-butyldimethylsiloxy)ethene
  参考文献：
  名称：

  Asymmetric Total Synthesis of TaxolR

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

文献信息

• Efficient Mannich Reaction Using Iminium Salts Generated from Glycine Derivatives
  作者：Makoto Shimizu、Toshiki Kusunoki、Mari Yoshida、Koichi Kondo、Isao Mizota

  DOI：10.1246/cl.2011.351

  日期：2011.4.5

  Iminium salts generated by the oxidation of amino ketene silyl acetals underwent a facile Mannich reaction with another ketene silyl acetal to give aspartic acid derivatives in good yields. The dia...

  由氨基烯酮甲硅烷基缩醛氧化生成的亚胺盐与另一种烯酮甲硅烷基缩醛进行简单的曼尼希反应，以良好的收率得到天冬氨酸衍生物。日...
• A New Efficient Method for Stereoselective Synthesis of 2-Deoxy-C-ribofuranosides
  作者：Teruaki Mukaiyama、Hiromi Uchiro、Noriyuki Hirano、Tatsuya Ishikawa

  DOI：10.1246/cl.1996.629

  日期：1996.8

  Stereoselective C-glycosylation of 2-deoxyribose derivatives having 3-O-thiocarbamoyl directing group with carbon nucleophiles was successfully carried out by using SiCl(OTf)3 as an activator. Several 2-deoxy-β-C-ribofuranosides which can be easily converted to 2′-deoxy-C-nucleosides were obtained in good yields with high stereoselectivities.

  成功地通过使用SiCl(OTf)3作为活化剂，对具有3-O-硫氨基甲酰基导向基的2-脱氧核糖衍生物进行了立体选择性的C-糖苷化反应，使用了碳亲核试剂。获得了几种2-脱氧-β-C-核糖呋喃苷，具有良好的产率和高的立体选择性，这些产物可以很容易转化为2′-脱氧-C-核苷。
• A novel Mannich-type reaction: Lanthanide triflate-catalyzed reactions of N-(α-aminoalkyl)benzotriazoles with silyl enolates
  作者：Shū Kobayashi、Haruro Ishitani、Susumu Komiyama、Daniela C. Oniciu、Alan R. Katritzky

  DOI：10.1016/0040-4039(96)00671-5

  日期：1996.5

  In the presence of a catalytic amount of a lanthanide triflate, N-(α-aminnoalkyl)benzotriazoles reacted with silyl enolates to give the corresponding β-amino ketone or ester derivatives in high yields with high diastereoselectivities.

  在催化量的三氟甲烷磺酸镧系元素的存在下，N-（α-氨基烷基）苯并三唑与甲硅烷基烯醇酸酯反应，以高收率和高的非对映选择性产生相应的β-氨基酮或酯衍生物。
• β-Amino acid substitutions and structure-based CoMFA modeling of hepatitis C virus NS3 protease inhibitors
  作者：Johanna Nurbo、Shane D. Peterson、Göran Dahl、U. Helena Danielson、Anders Karlén、Anja Sandström

  DOI：10.1016/j.bmc.2008.04.005

  日期：2008.5

  In an effort to develop a new type of HCV NS3 peptidomimetic inhibitor, a series of tripeptide inhibitors incorporating a mix of alpha- and beta-amino acids has been synthesized. To understand the structural implications of beta-amino acid substitution, the P-1, P-2, and P-3 positions of a potent tripeptide scaffold were scanned and combined with carboxylic acid and acyl sulfonamide C-terminal groups. Inhibition was evaluated and revealed that the structural changes resulted in a loss in potency compared with the a- peptide analogues. However, several compounds exhibited mu M potency. Inhibition data were compared with modeled ligand-protein binding poses to understand how changes in ligand structure affected inhibition potency. The P-3 position seemed to be the least sensitive position for beta-amino acid substitution. Moreover, the importance of a proper oxyanion hole interaction for good potency was suggested by both inhibition data and molecular modeling. To gain further insight into the structural requirements for potent inhibitors, a three-dimensional quantitative structure-activity relationship (3D- QSAR) model has been constructed using comparative molecular field analysis (CoMFA). The most predictive CoMFA model has q(2) = 0.48 and r(pred)(2) = 0.68. (C) 2008 Elsevier Ltd. All rights reserved.