3,4-bis-benzyloxy-2-benzyloxymethyl-3,4-dihydro-H-pyrrole 1-oxide | 880154-61-0

• 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: 3,4-bis-benzyloxy-2-benzyloxymethyl-3,4-dihydro-H-pyrrole 1-oxide
• 英文别名: (2S,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole-1-oxide；(2s,3r,4r)-3,4-Bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2h-pyrrole 1-oxide；(2S,3R,4R)-1-oxido-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyrrol-1-ium
• CAS: 880154-61-0
• 化学式: C₂₆H₂₇NO₄
• 分子量: 417.505
• InChiKey: FYVRCXABOYBHKY-JIMJEQGWSA-N

物化性质

• 沸点：
  612.1±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-bis-benzyloxy-2-benzyloxymethyl-3,4-dihydro-H-pyrrole 1-oxide 在 二碳酸二叔丁酯 、 氢气 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 1-amino-1,2,5-trideoxy-2,5-imino-D-glucitol
  参考文献：
  名称：

  Bioevaluation of sixteen ADMDP stereoisomers toward alpha-galactosidase A: Development of a new pharmacological chaperone for the treatment of Fabry disease and potential enhancement of enzyme replacement therapy efficiency

  摘要：

  A unique molecular library consisting of all sixteen synthetic ADMDP (1-aminodeoxy-DMDP) stereo-isomers has been prepared and evaluated for inhibitory activity against alpha-Gal A, and ability to impart thermal stabilization of this enzyme. The results of this testing led us to develop a novel pharmacological chaperone for the treatment of Fabry disease. 3-Epimer ADMDP was found to be an effective pharmacological chaperone, able to rescue alpha-Gal A activity in the lymphoblast of the N215S Fabry patient derived cell line, without impairment of cellular 0-galactosidase activity. When 3-epimer ADMDP was administered with rh-alpha-Gal A (enzyme replacement therapy) for the treatment of Fabry patient-derived cell lines, improvements in the efficacy of rh-alpha-Gal A was observed, which suggests this small molecule can also provide clinical benefit of enzyme replacement therapy in Fabry disease. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.07.025
• 作为产物：
  描述：

  (2R,3S,4S)-1,3,4-tris(benzyloxy)-5-oxopentan-2-yl methanesulfonate 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 以129 g的产率得到3,4-bis-benzyloxy-2-benzyloxymethyl-3,4-dihydro-H-pyrrole 1-oxide
  参考文献：
  名称：

  A Practical Synthesis of Sugar-Derived Cyclic Nitrones: Powerful Synthons for the Synthesis of Iminosugars

  摘要：

  从相应的醛糖通过一种高效实用的过程合成了糖源性环硝酮，该过程涉及七个步骤反应，整体产率为良好到优秀（10-42%）。这种合成策略只需使用廉价试剂，操作简单，因此适合大规模制备。

  DOI：

  10.1055/s-0029-1219189

文献信息

• An Entry to the Carbapenem Antibiotic Scaffold via the Asymmetric Kinugasa Reaction
  作者：Marek Chmielewski、Magdalena Maciejko、Sebastian Stecko、Olga Staszewska-Krajewska、Margarita Jurczak、Bartłomiej Furman

  DOI：10.1055/s-0032-1316732

  日期：——

  entry toward thienamycin and related compounds. The copper(I)-mediated reaction between five-membered cyclic nitrones and terminal acetylenes, leading to the assembly of the basic skeleton of carbapenem antibiotics is described. The diastereoselectivity of this cycloaddition–rearrangement cascade, a process known as the Kinugasa reaction, with respect to the structure and configuration of both substrates

  摘要 描述了五元环硝酮与末端乙炔之间的铜（I）介导的反应，导致碳青霉烯抗生素基本骨架的组装。讨论了这种环加成-重排级联的非对映选择性，该过程称为Kinugasa反应，涉及两种底物的结构和构型以及反应条件。所描述的方法在糖衍生的硝酮上的应用为硫霉素和相关化合物提供了有吸引力的入口。 描述了五元环硝酮与末端乙炔之间的铜（I）介导的反应，导致碳青霉烯抗生素基本骨架的组装。讨论了这种环加成-重排级联的非对映选择性，该过程称为Kinugasa反应，涉及两种底物的结构和构型以及反应条件。所描述的方法在糖衍生的硝酮上的应用为硫霉素和相关化合物提供了有吸引力的入口。
• Transition-Metal-Catalyzed Ring Expansion of Diazocarbonylated Cyclic <i>N</i>-Hydroxylamines: A New Approach to Cyclic Ketonitrones
  作者：Evelyn Lieou Kui、Alice Kanazawa、Jean-François Poisson、Sandrine Py

  DOI：10.1021/ol502029z

  日期：2014.9.5

  Novel C-ethoxycarbonyl cyclic ketonitrones are synthesized from the Ag- or Cu-catalyzed ring expansion of β-diazo cyclic hydroxylamines. The latter are themselves easily obtained by the addition of lithiated ethyl diazoacetate onto cyclic nitrones. The regioselective metal-catalyzed rearrangement of β-diazo cyclic hydroxylamines proved highly efficient and resulted in a synthetically useful ring expansion

  由Ag或Cu催化的β-重氮环羟胺的扩环合成了新型的C-乙氧羰基环状酮硝酮。后者本身很容易通过将锂化的重氮乙酸乙酯加到环状硝酮上而获得。β-重氮环羟胺的区域选择性金属催化的重排被证明是高效的，并导致合成上有用的环扩展以产生6或7元环官能化的硝酮。这两个步骤的结果，即亲和性地将α-重氮酸酯加成到硝酮上和扩环，是正式的硝酮同系物。
• The use of carbonyl group anisotropy effect in determination of the relative configuration of carbapenams
  作者：Olga Staszewska-Krajewska、Wojciech Bocian、Magdalena Maciejko、Piotr Szcześniak、Krzysztof Szymczak、Marek Chmielewski、Bartłomiej Furman

  DOI：10.3998/ark.5550190.p008.450

  日期：——

  shifts of the H-2 proton and geminal protons of the protected alkoxymethyl group at the C-2 carbon atom. The differences of 1 H NMR chemical shifts of these protons fall in two ranges of about 3.3-3.7 ppm, and 4.0-4.4 ppm. This observation can be attributed to the influence of the anisotropy of the neighboring carbonyl group and can be easily correlated with configuration at the bridgehead carbon atom

  通过分析 C-2 碳上受保护的烷氧基甲基的 H-2 质子和孪生质子的化学位移，可以很容易地确定在 Kinugasa 反应中获得的双环碳青霉烯的桥头碳原子处新形成的立体中心的相对构型原子。这些质子的 1 H NMR 化学位移的差异落在约 3.3-3.7 ppm 和 4.0-4.4 ppm 的两个范围内。这种观察可以归因于相邻羰基各向异性的影响，并且可以很容易地与桥头碳原子的构型相关联。
• Synthetic Utility of Sugar-Derived Cyclic Nitrones: A Diastereoselective Synthesis of Linear 4-Azatriquinanes
  作者：Krishna Kaliappan、Anandaraju Bandaru

  DOI：10.1055/s-0031-1290375

  日期：2012.6

  A diastereoselective Pauson–Khand reaction has been utilized as the key step in the construction of azatriquinanes from sugar-derived nitrones.

  非对映选择性 Pauson-Khand 反应已被用作从糖衍生的硝酮构建 azatriquinanes 的关键步骤。
• A Stereoselective Route to Aza-<i>C</i>-aryl Glycosides from Arynes and Chiral Nitrones
  作者：Rama Kanwar Khangarot、Krishna P. Kaliappan

  DOI：10.1002/ejoc.201200685

  日期：2012.10

  organic synthesis. These highly-reactive, strained and kinetically unstable species have numerous applications in synthetic chemistry. In this article, a highly-diasteroselective and efficient 1,3-dipolar cycloaddition reaction between a range of arynes and sugar-derived cyclic nitrones leading to an interesting class of sugar-based benzo[d]isoxazolines is described. These benzo[d]isoxazolines upon selective

  芳炔被认为是有机合成中潜在的多功能中间体。这些高反应性、应变和动力学不稳定的物质在合成化学中有许多应用。在这篇文章中，描述了一系列芳烃和糖衍生的环状硝酮之间的高度非对映选择性和高效的 1,3-偶极环加成反应，导致了一类有趣的糖基苯并 [d] 异恶唑啉。这些苯并[d]异恶唑啉在选择性N-O键断裂后以良好的产率提供各种取代的氮杂-C-芳基糖苷。这些取代的吡咯烷衍生物是手性氨基酚，可能是不对称合成中潜在的手性配体和有机催化剂。