[2-(benzyloxy-diisopropylamino-phosphanyloxy)-ethyl]-carbamic acid benzyl ester | 162406-70-4

• 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: [2-(benzyloxy-diisopropylamino-phosphanyloxy)-ethyl]-carbamic acid benzyl ester
• 英文别名: benzyl (2-(((benzyloxy)(diisopropylamino)phosphanyl)oxy)ethyl)carbamate；benzyl N-[2-[[di(propan-2-yl)amino]-phenylmethoxyphosphanyl]oxyethyl]carbamate
• CAS: 162406-70-4
• 化学式: C₂₃H₃₃N₂O₄P
• 分子量: 432.5
• InChiKey: ZYOCOCOAFNUMEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  495.7±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  60
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2-(benzyloxy-diisopropylamino-phosphanyloxy)-ethyl]-carbamic acid benzyl ester 在 四氮唑 、 盐酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2-{benzyloxy-[(2R,3R)-2,3-dihydroxy-4-(4'-methoxybenzyloxymethyl)-butoxy]-phosphoryloxy}-ethyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of Hybrid Lipid Probes:  Derivatives of Phosphatidylethanolamine-Extended Phosphatidylinositol 4,5-Bisphosphate (Pea-PIP₂)

  摘要：

  The total asymmetric synthesis of a novel hybrid lipid possessing a 2,3-diacylthreitol backbone, rather than a 1,2-diacylglycerol backbone, is described. The title compound, Pea-PIP2, possesses a phosphatidylethanolamine (PE) headgroup at the 1-position and a phosphatidylinositol 4,5-bisphosphate (Ptdlns(4,5)P-2) headgroup, at the 4-position. Reporters (biotin, fluorophores, spin label) were covalently attached to the free amino group of the PE, such that these reporters were targeted to the lipid-water interface. The diacyl moieties allow incorporation of Pea-PIP2 into a lipid bilayer, while the PtdIns(4,5)P-2 moiety in the aqueous layer was specifically recognized by PtdIns(4,5)P-2-specific binding proteins.

  DOI：

  10.1021/jo011185a
• 作为产物：
  描述：

  氯甲酸苄酯 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 [2-(benzyloxy-diisopropylamino-phosphanyloxy)-ethyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  [EN] BIPOLAR TETRAETHER LIPIDS
  [FR] LIPIDES BIPOLAIRES DE TYPE TÉTRAÉTHER

  摘要：

  披露的内容包括但不限于化合物、组合物、脂质体及其方法。

  公开号：

  WO2017040702A1

文献信息

• A new approach to construct full-length glycosylphosphatidylinositols of parasitic protozoa and [4-deoxy-Man-III]-GPI analogues
  作者：Asif Ali、D. Channe Gowda、Ram A. Vishwakarma

  DOI：10.1039/b414119a

  日期：——

  A new [2 + 2 + 2] approach to construct GPI molecules through the efficient synthesis of glucosamine-inositol and tetramannose intermediates led to a total synthesis of a GPI-anchor of Trypanosoma cruzi, and also afforded a key intermediate for the synthesis of valuable [4-deoxy-Man-III]-GPI analogues.

  通过高效合成葡糖胺-肌醇和四甘露糖中间体，一种新的[2+2+2]方法构建GPI分子，实现了Trypanosoma cruzi的GPI锚的完全合成，并提供了一种合成有价值[4-脱氧-甘露糖-III]-GPI类似物所需的关键中间体。
• Chemical Synthesis of Helicobacter pylori Lipopolysaccharide Partial Structures and their Selective Proinflammatory Responses
  作者：Atsushi Shimoyama、Akinori Saeki、Natsuko Tanimura、Hiroko Tsutsui、Kensuke Miyake、Yasuo Suda、Yukari Fujimoto、Koichi Fukase

  DOI：10.1002/chem.201003581

  日期：2011.12.16

  Helicobacter pylori is a common cause of gastroduodenal inflammatory diseases such as chronic gastritis and peptic ulcers and also an important factor in gastric carcinogenesis. Recent reports have demonstrated that bacterial inflammatory processes, such as stimulation with H. pylori lipopolysaccharide (LPS), initiate atherosclerosis. To establish the structures responsible for the inflammatory response

  幽门螺杆菌是胃十二指肠炎的常见病因，例如慢性胃炎和消化性溃疡，也是胃癌发生的重要因素。最近的报道表明，细菌的炎症过程，例如用幽门螺杆菌脂多糖（LPS）刺激，会引发动脉粥样硬化。为了建立负责幽门螺杆菌LPS炎症反应的结构，我们合成了各种脂质A结构（即三酰化脂质A和Kdo-脂质A化合物），在1磷酸部分具有或不具有乙醇胺基，通过一条新的分歧合成路线。Kdo N的立体选择性α-糖基化通过使用微流控方法获得了苯基三氟乙酰亚胺酸酯。脂质A和Kdo-脂质A化合物均不是IL-1β，IL-6或IL-8的强诱导剂，这表明幽门螺杆菌LPS不能诱导急性炎症。实际上，除了具有乙醇胺基团的脂质A化合物显示出非常弱的激动活性外，脂质A和Kdo-脂质A化合物对大肠杆菌LPS诱导的细胞因子具有拮抗活性。另一方面，这些幽门螺杆菌的LPS部分结构显示出有效的IL-18和IL-12诱导活性。IL-18已被证明与慢性炎症相关，所以
• Catalytic synthesis of enantiopure mixed diacylglycerols – synthesis of a major M. tuberculosis phospholipid and platelet activating factor
  作者：Peter Fodran、Adriaan J. Minnaard

  DOI：10.1039/c3ob41483c

  日期：——

  An efficient catalytic one-pot synthesis of TBDMS-protected diacylglycerols has been developed, starting from enantiopure glycidol. Subsequent migration-free deprotection leads to stereo- and regiochemically pure diacylglycerols. This novel strategy has been applied to the synthesis of a major Mycobacterium tuberculosis phospholipid, its desmethyl analogue, and platelet activating factor.

  一种高效催化的一锅法合成TBDMS保护的二酰基甘油已被开发出来，从手性纯甘油酸环丙烷开始，随后无迁移的脱保护步骤产生立体化学和区域化学纯的二酰基甘油。这种新颖的策略已应用于合成主要的结核分枝杆菌磷脂、其脱甲基类似物和血小板活化因子。
• Effect of Headgroups on Small-Ion Permeability across Archaea-Inspired Tetraether Lipid Membranes
  作者：Takaoki Koyanagi、Geoffray Leriche、Alvin Yep、David Onofrei、Gregory P. Holland、Michael Mayer、Jerry Yang

  DOI：10.1002/chem.201601326

  日期：2016.6.6

  1‐palmitoyl‐2‐oleoyl‐sn‐glycerol (PO) lipids varied by as much as 32‐fold within the same series of headgroups. These results demonstrate that membrane leakage from GMGT lipids is less influenced by headgroup structure, making it possible to tailor the structure of the polar headgroups on GMGT lipids while retaining predictable leakage properties of membranes comprised of these tethered lipids.

  本文研究了四种不同极性头基对古细菌启发的甘油单烷基甘油四醚（GMGT）脂质组成的脂质体对小离子膜通透性的影响。我们发现，跨GMGT脂膜的膜泄漏率随头基结构的变化而变化≤1.6。但是，在相同的头组中，小离子跨膜的商业渗漏率由形成双层的1-棕榈酰基-2-油酰基-sn-甘油（PO）脂质组成。这些结果表明，从GMGT脂质泄漏的膜受到头基结构的影响较小，这使得可以在GMGT脂质上修饰极性头基的结构，同时保留了由这些束缚脂质组成的膜的可预测的泄漏性能。
• Synthesis of 3-O- and 4-O-(2-aminoethylphosphono) derivatives of methyl l-glycero-α-d-manno-heptopyranoside
  作者：Martin Walter、Claudia Kohout、Markus Blaukopf、Paul Kosma

  DOI：10.1007/s00706-016-1868-6

  日期：2017.1

  ABSTRACT: Phosphoethanolamine derivatives of the bacterial saccharide l-glycero-d-manno-heptose have been prepared using a phosphoramidite-based coupling reaction at position 4 of a side-chain-protected 2,3-O-orthoester methyl heptoside and at position 3 of a 3,4-diol heptoside, respectively. Global deprotection afforded the corresponding 2-aminoethylphosphodiester derivatives as substrates for crystallographic

  摘要：利用基于亚磷酰胺的偶联反应，在侧链保护的 2,3-O-原酸酯甲基庚糖苷的 4 位和 3 位上制备了细菌糖 L-甘油-d-甘露庚糖的磷酸乙醇胺衍生物。分别是3,4-二醇庚苷。整体脱保护提供了相应的 2-氨基乙基磷酸二酯衍生物作为底物，用于针对细菌脂多糖内核结构的凝集素和抗体的晶体学和结合研究。图形概要：