Octadecanoic acid (R)-2-(benzyloxy-diisopropylamino-phosphanyloxy)-1-octadecanoyloxymethyl-ethyl ester | 195970-40-2

• 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: Octadecanoic acid (R)-2-(benzyloxy-diisopropylamino-phosphanyloxy)-1-octadecanoyloxymethyl-ethyl ester
• 英文别名: [(2R)-3-[[di(propan-2-yl)amino]-phenylmethoxyphosphanyl]oxy-2-octadecanoyloxypropyl] octadecanoate
• CAS: 195970-40-2
• 化学式: C₅₂H₉₆NO₆P
• 分子量: 862.311
• InChiKey: SLSSIOAUXFJAQP-BQWYIOEMSA-N

物化性质

• 沸点：
  778.4±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  20
• 重原子数：
  60
• 可旋转键数：
  46
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  、 Octadecanoic acid (R)-2-(benzyloxy-diisopropylamino-phosphanyloxy)-1-octadecanoyloxymethyl-ethyl ester 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  开发富含同位素的磷脂酰肌醇 4 和 5 磷酸细胞质谱探针

  摘要：

  合成磷脂酰肌醇磷酸酯 (PtdIns P n ) 衍生物在拓宽我们对 PtdIns P n代谢的理解方面发挥着关键作用。然而，此类工具的开发依赖于有效的对映选择性和区域选择性合成策略。在这里，我们报告了适用于合成氘化 PtdIns4 P和 PtdIns5 P衍生物的不同合成路线的发展。开发的合成策略涉及使用 Lipozyme TL-IM® 的关键酶解对称步骤。此外，我们优化了氘代肌醇的大规模合成，允许制备一系列饱和和不饱和的氘代PtdIns4 P和 PtdIns5 P衍生物。在 MCF7 细胞中进行的实验表明，这些氘化探针能够量化细胞环境中相应的内源性磷脂。总的来说，这些氘化探针将成为帮助我们更好地了解 PtdIns P n在生理学和疾病中所起作用的强大工具。

  DOI：

  10.1039/d0sc06219g
• 作为产物：
  描述：

  1-O-stearoyl-3-O-benzyl-sn-glycerol 在 palladium on activated charcoal 四氮唑 、 4-二甲氨基吡啶 、 氢气 作用下， 以 吡啶 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 Octadecanoic acid (R)-2-(benzyloxy-diisopropylamino-phosphanyloxy)-1-octadecanoyloxymethyl-ethyl ester
  参考文献：
  名称：

  Phosphorylation of Unnatural Phosphatidylinositols with Phosphatidylinositol 3-Kinase

  摘要：

  Phosphatidylinositol analogs (PIC2PIC18) having a series of saturated fatty acid (C2-C18) at sn-2 position were synthesized and subjected to the phosphorylation reaction with phosphatidylinositol 3-kinase (PI 3-kinase). The reactivity of PIC8 with PI 3-kinase turned out to be comparable to that of natural PI, although PIC18 was not phosphorylated under the same condition. The chirality of sn-2 center was not responsible for the phosphorylation reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00161-7

文献信息

• Efficient Asymmetric Synthesis of Phosphatidyl-D-myo-inositol 3,4,5-trisphosphate.
  作者：Takayuki SAWADA、Ryuichi SHIRAI、Shigeo IWASAKI

  DOI：10.1248/cpb.45.1521

  日期：——

  Phosphatidyl-D-myo-inositol 3, 4, 5-trisphosphate, a candidate of the second messenger in cellular signal transduction, was efficiently synthesized in a homochiral form.

  细胞信号转导中的第二信使候选物质磷脂酰-D-肌醇-3,4,5-三磷酸以同手性形式被高效合成。
• [EN] SYNTHETIC MOLECULES HAVING IMMUNE ACTIVITY<br/>[FR] MOLECULES SYNTHETIQUES A IMMUNO-ACTIVITE
  申请人：MALAGHAN INST OF MEDICAL RES

  公开号：WO2005049631A1

  公开（公告）日：2005-06-02

  The present invention is directed to synthetic molecules having biological activity similar to PIM (acyl glycerol phosphatidylinositol manno-oligosaccharide) activity, for use in the treatment and prevention of inflammatory or immune cell mediated diseases or disorders.

  本发明涉及具有类似于PIM（酰基甘油磷脂肌醇寡糖）活性的合成分子，用于治疗和预防炎症性或免疫细胞介导的疾病或紊乱。
• Efficient Chemical Synthesis of a Dodecasaccharidyl Lipomannan Component of Mycobacterial Lipoarabinomannan
  作者：Bert Fraser-Reid、Siddhartha Ray Chaudhuri、K. N. Jayaprakash、Jun Lu、Changalvala V. S. Ramamurty

  DOI：10.1021/jo802000p

  日期：2008.12.19

  Lipomannan (LM) is one of the domains of lipoarabinomannan (LAM) glycolipids, the latter being one of several cell surface organic molecules that fortify mycobacterial species against external attack. Some members of mycobacterial families are pathogenic, most notably Mycobacterium tuberculosis and Mycobacterium leprae, while others are nonpathogenic, and used in the clinic, such as Mycobacterium smegmatis. Additional biological significance arises from the fact that LM has been implicated in several health disorders outside of those associated with mycobacterial pathogens, notably for treatment of bladder cancer. LM is comprised of a heavily lipidated phosphoinositide dimannoside headgroup, from which a mannan array, of varied complexity, extends. The latter consists of a 1,6-alpha-linked backbone flanked at position O2, not necessarily regularly, with alpha-linked mannosides. This paper gives an example of lipomannan synthesis in which all of the sugar components, whether functioning as donors or acceptors, are obtained from n-pentenyl orthoesters, themselves in turn prepared in three easy steps from D-mannose. Assembly of the mannan array is facilitated by the exquisite regioselectivity occasioned by the use of ytterbium triflate/N-iodosuccinimide as the trigger for reaction of n-pentenyl orthoesters.
• A PIM2 analogue suppresses allergic airway disease
  作者：Jacquie L. Harper、Colin M. Hayman、David S. Larsen、Gavin F. Painter、Gurmit Singh-Gill

  DOI：10.1016/j.bmc.2010.11.058

  日期：2011.1

  Two approaches for the synthesis of a phosphatidylinositol dimannoside (PIM2) analogue 4 that mimics the suppressive activity of natural PIMs and also synthetic PIM2 have been developed. This analogue, where the inositol core was replaced by glycerol, was tested for its ability to suppress cellular inflammation in a mouse model of allergic asthma and shown to be effective in suppressing airway eosinophilia. Suppression of all inflammatory cells monitored was observed, indicating a general blockade of cellular activity. These data indicate that the inositol core is not essential for this suppressive activity. (C) 2010 Elsevier Ltd. All rights reserved.
• The structural requirement of phosphatidylinositols as substrate of phosphatidylinositol 3-kinase
  作者：Ryuichi Shirai、Koji Morita、Asuka Nishikawa、Noriyuki Nakatsu、Yasuhisa Fukui、Naoko Morisaki、Yuichi Hashimoto

  DOI：10.1016/s0040-4039(99)00004-0

  日期：1999.2

  Synthetic distearate phosphatidylinositol (PI) was not phosphorylated by PI 3-kinase. The fatty acids at glycerol sn-2 must be as short as octanoic acid or less to act as a substrate of PI 3-kinase. (C) 1999 Elsevier Science Ltd. All rights reserved.