2-amino-4-(tert-butyldimethylsilyloxy)butanoic acid

• 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: 2-amino-4-(tert-butyldimethylsilyloxy)butanoic acid
• 英文别名: O-(tert-Butyldimethylsilyl)-L-homoserine；2-amino-4-[tert-butyl(dimethyl)silyl]oxybutanoic acid
• 化学式: C₁₀H₂₃NO₃Si
• 分子量: 233.383
• InChiKey: BKFGDICOIJEWPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-4-(tert-butyldimethylsilyloxy)butanoic acid 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 草酰氯 、 sodium hydride 、 caesium carbonate 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 37.0h， 生成 6-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-1-[(4-chlorophenyl)methyl]-4,7-dimethyl-2-[3-(trifluoromethoxy)phenoxy]-1H,4H,5H,6H,7H,8H-imidazo[4,5-e][1,4]diazepine-5,8-dione
  参考文献：
  名称：

  WO2019173327A5

  摘要：

  公开号：

  WO2019173327A5
• 作为产物：
  描述：

  DL-高丝氨酸 、 叔丁基二甲基氯硅烷 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以88%的产率得到2-amino-4-(tert-butyldimethylsilyloxy)butanoic acid
  参考文献：
  名称：

  Stereoselective synthesis of 2,4,5-trisubstituted piperidines by carbonyl ene and Prins cyclisations

  摘要：

  报告了一种合成2,4,5-三取代哌啶的方法，其中关键步骤是醛类化合物1的Prins或羰基烯环化反应。在-78°C下，采用浓盐酸催化的CH2Cl2中进行的Prins环化反应，获得了四种可能的立体异构体中的两种良好产率，其中4,5-顺式产物7的产率在立体异构体比率上高达94:6。随着2-取代基体积的增大，环化反应的立体选择性降低，对于体积非常大的2-取代基体则变得无选择性。相比之下，在20–60°C的CH2Cl2或CHCl3中，MeAlCl2催化的环化反应则偏向于4,5-反式立体异构体8，其立体异构体比率高达99:1。由HCl催化的低温环化反应在动力学控制下进行，机制涉及显著的碳正离子特性，其中，4,5-顺式阳离子由于与相邻氧的重叠而比4,5-反式阳离子更稳定。而由MeAlCl2催化的环化反应则在热力学控制下进行，生成的产物中4-和5-取代基均为赤面配置。

  DOI：

  10.1039/b808644c

文献信息

• Synthesis of Oxazolidin-2-ones and Imidazolidin-2-ones Directly from 1,3-Diols or 3-Amino Alcohols using Iodobenzene Dichloride and Sodium Azide
  作者：Tian He、Wen-Chao Gao、Wei-Kun Wang、Chi Zhang

  DOI：10.1002/adsc.201300982

  日期：2014.3.24

  A general and efficient method for the synthesis of oxazolidin‐2‐ones and imidazolidin‐2‐ones directly from 1,3‐diols and 3‐amino alcohols has been developed using the same reagent combination of iodobenzene dichloride (PhICl2) and sodium azide (NaN3).

  使用碘代二氯二苯甲烷（PhICl 2）和叠氮化钠的相同试剂组合，开发了一种直接，直接由1,3-二醇和3-氨基醇合成恶唑烷-2-酮和咪唑啉-2-酮的通用有效方法。（NaN 3）。
• Melanocortin receptor ligands
  申请人：The Procter & Gamble Company

  公开号：US20040224985A1

  公开（公告）日：2004-11-11

  Disclosed are MC-3/MC-4 receptor ligands, the ligands having the following formula: 1 wherein A is a conformationally restricted ring system selected from the group consisting of: a) non-aromatic carbocyclic rings; b) aromatic carbocyclic rings; c) non-aromatic heterocyclic rings; d) aromatic heterocyclic rings; wherein said rings comprises from 5 to 8 atoms; and W is a unit which preferable comprises D-1-fluorophenyalanine, Y comprises a heteroatom, and Z comprises an aromatic carbocyclic ring. Also disclosed are pharmaceutical compositions comprising the ligands of the invention as well as methods of treating diseases mediated through MC-3/MC-4 receptors.

  本发明涉及MC-3/MC-4受体配体，该配体具有以下公式：1其中A是从以下群组中选择的构象限制环系统：a）非芳香烷环；b）芳香烷环；c）非芳香杂环；d）芳香杂环；其中所述环包含5到8个原子；W是一个单元，它最好包括D-1-氟苯丙氨酸，Y包括一个杂原子，Z包括一个芳香烷环。本发明还涉及包含所述配体的制药组合物，以及通过MC-3/MC-4受体介导的治疗疾病的方法。
• Synthesis of Natural Product-Inspired Inhibitors of <i>Mycobacterium tuberculosis</i> Mycothiol-Associated Enzymes: The First Inhibitors of GlcNAc-Ins Deacetylase
  作者：Belhu B. Metaferia、Brandon J. Fetterolf、Syed Shazad-ul-Hussan、Matthew Moravec、Jeremy A. Smith、Satyajit Ray、Maria-Teresa Gutierrez-Lugo、Carole A. Bewley

  DOI：10.1021/jm070669h

  日期：2007.12.13

  Synthesis and evaluation of a chemical library of inhibitors of the mycothiol biosynthesis enzyme GlcNAc-Ins deacetylase (MshB) and the mycothiol-dependent detoxification enzyme mycothiol-S-conjugate amidase (MCA) from Mycobacterium tuberculosis are reported. The library was biased to include structural features of a group of natural products previously shown to competitively inhibit MCA. Molecular docking studies that reproducibly placed the inhibitors in the active site of the enzyme MshB reveal the mode of binding and are consistent with observed biological activity.
• Potent, Novel in Vitro Inhibitors of the <i>Pseudomonas </i><i>a</i><i>eruginosa</i> Deacetylase LpxC
  作者：Toni Kline、Niels H. Andersen、Eric A. Harwood、Jason Bowman、Andre Malanda、Stephanie Endsley、Alice L. Erwin、Michael Doyle、Susan Fong、Alex L. Harris、Brian Mendelsohn、Khisimuzi Mdluli、Christian R. H. Raetz、C. Kendall Stover、Pamela R. Witte、Asha Yabannavar、Shuguang Zhu

  DOI：10.1021/jm010579r

  日期：2002.7.1

  Deacetylation of uridyldiphospho-3-O-(R-hydroxydecanoyl)-N-acetylglucosamine by LpxC is the first committed step in the Pseudomonas aeruginosa biosynthetic pathway to lipid A; homologous enzymes are found widely among Gram-negative bacteria. As an essential enzyme for which no inhibitors have yet been reported, the P. aeruginosa LpxC represents a highly attractive target for a novel antibacterial drug. We synthesized several focused small-molecule libraries, each composed of a variable aromatic ring, one of four heterocyclic/spacer moieties, and a hydroxamic acid and evaluated the LpxC inhibition of these compounds against purified P. aeruginosa enzyme. To ensure that the in vitro assay would be as physiologically relevant as possible, we synthesized a tritiated form of the specific P. aeruginosa glycolipid substrate and measured directly the enzymatically released acetate. Several of our novel compounds, predominantly those having fluorinated substituents on the aromatic ring and an oxazoline as the heterocyclic moiety, demonstrated in vitro IC50 values less than 1 muM. We now report the synthesis and in vitro evaluation of these P. aeruginosa LpxC inhibitors.
• WO2019173327A5
  申请人：——

  公开号：WO2019173327A5

  公开（公告）日：2022-03-14