1-O-(tert-Butyldiphenylsilyl)-2,3:5,6-di-O-isoproylidene-myo-inositol | 119874-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-(tert-Butyldiphenylsilyl)-2,3:5,6-di-O-isoproylidene-myo-inositol
• 英文别名: 1-O-(tert-butyldiphenylsilyl)-2,3:5,6-di-O-isopropylidene-D-myo-inositol；1(3)-O-(tert-butyldiphenylsilyl)-2,3(1):5,6(4)-di-O-isopropylidene-D-myo-inositol；1-O-tert-butyldiphenylsilyl-2,3:5,6-di-O-isopropylidene-D-myo-inositol；1-O-t-butyldiphenylsilyl-2,3:5,6-di-O-isopropylidene-myo-inositol
• CAS: 119874-35-0；119943-93-0；124648-22-2
• 化学式: C₂₈H₃₈O₆Si
• 分子量: 498.692
• InChiKey: SFPIFESXSAQLCS-KMWHABIXSA-N

物化性质

• 熔点：
  52-54°C
• 溶解度：
  可溶于氯仿、可溶于二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-O-(tert-Butyldiphenylsilyl)-2,3:5,6-di-O-isoproylidene-myo-inositol 在 四丁基氟化铵 、 苯甲基-2-磺酰三硝基三氮唑 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 生成
  参考文献：
  名称：

  Improved syntheses of inositol phospholipid analogues

  摘要：

  DOI：

  10.1016/s0040-4039(01)93785-2
• 作为产物：
  描述：

  1-O-(tert-butyldiphenylsilyl)-4-O-camphanyl-2,3:5,6-di-O-isopropylidene-D-myo-inositol 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以94%的产率得到1-O-(tert-Butyldiphenylsilyl)-2,3:5,6-di-O-isoproylidene-myo-inositol
  参考文献：
  名称：

  1,2-二棕榈酰基-甘油-3-基---肌醇1-磷酸酯的合成。

  摘要：

  提出了合成纯的1,2-二棕榈酰-sn-甘油-3-基-肌醇1-磷酸酯的简便方法。

  DOI：

  10.1016/s0040-4039(00)82254-6

文献信息

• Synthesis and Cellular Labeling of Multifunctional Phosphatidylinositol Bis‐ and Trisphosphate Derivatives
  作者：Rainer Müller、Ana Kojic、Mevlut Citir、Carsten Schultz

  DOI：10.1002/anie.202103599

  日期：2021.9

  We synthesized the first multifunctionalized phosphoinositide polyphosphate derivatives featuring a photo-removable protecting group (“cage”), a photo-crosslinkable diazirine group, and a terminal alkyne group useful for click chemistry. We demonstrate that the lipid derivatives readily enter cells. After photo-crosslinking, cell fixation and fluorescent tagging via click chemistry, we determined the

  我们合成了第一个多功能化的磷酸肌醇多磷酸衍生物，具有可光去除的保护基团（“笼”）、可光交联的二氮丙啶基团和可用于点击化学的末端炔基。我们证明脂质衍生物很容易进入细胞。经过光交联、细胞固定和通过点击化学进行荧光标记后，我们确定了脂质释放前后脂质衍生物的细胞内位置。我们发现 PI(3,4)P 2和 PI(3,4,5)P 3衍生物快速转运至质膜，开启了这些脂质参与主动转运的有趣可能性。我们利用光交联和点击化学功能来分析PI(3,4,5)P 3结合蛋白的蛋白质组。从后者，我们通过 RNAi 验证了假定的脂质结合蛋白 ATP11A 和 MPP6 参与 PI(3,4,5)P 3向质膜的转运。
• Total synthesis of the four stereoisomers of dihexadecanoyl phosphatidylinositol and the substrate stereospecificity of human erythrocyte membrane phosphatidylinositol 4-kinase
  作者：Rodney C. Young、C. Peter Downes、Drake S. Eggleston、Martin Jones、Colin H. Macphee、Kishore K. Rana、John G. Ward

  DOI：10.1021/jm00164a027

  日期：1990.2

  substrates for a partially purified phosphatidylinositol 4-kinase (EC 2.7.1.67) derived from human erythrocyte membranes revealed that the chirality of the inositol ring is crucial for efficient phosphorylation, whereas the chirality of the glycerol moiety is relatively unimportant. Moreover, the similarity in phosphorylation rates of the naturally occurring mammalian phospholipid, I, and its synthetic stereochemical

  已经开发了一种新的方便的方法来制备二十六烷酰基磷脂酰肌醇的四种立体异构体。以高收率合成对映体对酸不稳定，受五保护的肌醇构件，并将其与手性苯基二十六烷酰基甘油基磷酸酯偶联，得到完全保护的磷脂酰肌醇。随后通过在乙醇水溶液中的氢解和自水解作用将它们脱保护，得到所需的纯产物。比较这些化合物作为衍生自人红细胞膜的部分纯化的磷脂酰肌醇4-激酶（EC 2.7.1.67）的潜在底物的过程表明，肌醇环的手性对于有效的磷酸化至关重要，而甘油部分的手性相对不重要。此外，
• Improved synthesis of myo-inositol 1-(4-nitrophenyl hydrogen phosphate), a chromogenic substrate for phosphatidylinositol-specific phospholipase C
  作者：Aleksey V. Rukavishnikov、Tatiana O. Zaikova、O.Hayes Griffith、John F.W. Keana

  DOI：10.1016/s0009-3084(97)00069-8

  日期：1997.10

  This paper describes an improved procedure for the synthesis of racemic myo-inositol 1-(4-nitrophenyl hydrogen phosphate) (NPIP) a useful substrate for the continuous spectrophotometric assay of phosphatidylinositol-specific phospholipase C (PI-PLC). (C) 1997 Elsevier Science Ireland Ltd.
• Inhibition of human erythrocyte membrane phosphatidylinositol 4-kinase by phospholipid analogues
  作者：RC Young、CP Downes、M Jones、KJ Milliner、KK Rana、JG Ward

  DOI：10.1016/0223-5234(94)90146-5

  日期：1994.1

  Analogues of phosphatidylinositol (Ptdlns, 1) have been synthesized to investigate the structural requirements for inhibition of a Ptdlns 4-kinase obtained from human erythrocyte membranes. While the presence of either D-1 or D-3 Stereochemistry in the inositol moiety greatly influences the degree of inhibition produced by Ptdlns analogues, the stereochemistry of the glycerol moiety is of little consequence. Neither structural feature, however, makes a significant contribution to binding affinity. Competitive inhibitory activity was found to be retained (or even enhanced) in substantially simpler analogues consisting of 1 or 2 hydrocarbon chains attached to a charged phosphate head group, such as in the phosphatidic acids, 24 and 26. The observation that the phosphatidylinositol 4-phosphate (Ptdlns 4P) and phosphatidic acid analogues (eg, 16 or 17, and 26 respectively) inhibit Ptdlns 4-kinase may suggest that such species have a regulatory role in Ptdlns turnover.
• Synthesis of a new fluorogenic substrate for the continuous assay of mammalian phosphoinositide-specific phospholipase C
  作者：Aleksey V. Rukavishnikov、Tatiana O. Zaikova、G.Bruce Birrell、John F.W. Keana、O. Hayes Griffith

  DOI：10.1016/s0960-894x(99)00166-3

  日期：1999.4

  The synthesis of a fluorogenic substrate for mammalian phosphoinositide-specific phospholipase C is described. The substrate, based on the widely used fluorescein molecule? is a water-soluble substrate analog of phosphatidylinositol-4-phosphate. The fluorogenic substrate 2 is shown to be a sensitive substrate for human PI-PLC-delta 1 in a continuous assay. (C) 1999 Elsevier Science Ltd. All rights reserved.