DL-1-O-tert-butyldiphenylsilyl-myo-inositol | 142534-54-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: DL-1-O-tert-butyldiphenylsilyl-myo-inositol
• 英文别名: 1D-1-O-(tert-butyldiphenylsilyl)-myo-inositol；1D-(1-tert-butyldiphenylsilyl)-myo-inositol；1D-1-O-tert-butyldiphenylsilyl-myo-inositol
• CAS: 142534-54-1
• 化学式: C₂₂H₃₀O₆Si
• 分子量: 418.562
• InChiKey: XNBDWNDGDUVYIV-JMPUJIDWSA-N

物化性质

• 沸点：
  501.3±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.25
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  110.38
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  DL-1-O-tert-butyldiphenylsilyl-myo-inositol 在 吡啶 、 咪唑 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 1D-2,5,6-tris(methoxymethylene)-myo-inositol
  参考文献：
  名称：

  对映异构纯和区域特异性保护的肌醇的有效和系统合成

  摘要：

  各种对映体纯的和区域特异性保护的肌醇的有效和系统合成已经开发出来，这些肌醇可以很容易地用作大多数天然和非天然肌醇衍生物的前体。关键策略是使用樟脑作为保护基团和手性助剂，并在各个步骤中进行区域特异性控制。非对映体纯 1 ~-2,3-O(l'R,2'R,4'R-1',7',7'-trimethyl(2.2.1) bicyclohept-2'-ylidene)-myo-inositol (la)通过用D-樟脑二甲基乙缩醛使肌醇缩醛化然后从甲醇中结晶以3 1%的产率获得。在路线 A 中，四醇 1a 与叔丁基二苯基甲硅烷基氯 (TBDPS-C1) 的甲硅烷基化仅提供 1-OTBDPS-4,5,6-三醇 7，其充当关键中间体。其他试剂的进一步保护，彻底或区域特异性，结合选择性脱保护步骤，导致受保护的肌醇在 1-, 5-, 6-, 1,4-, 43-, 5,6-, 1, 4,5-和 1,4,6-位。在路线

  DOI：

  10.1021/ja00042a011
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 咪唑 、 三氟化硼乙醚 、 2-巯基乙醇 作用下， 生成 DL-1-O-tert-butyldiphenylsilyl-myo-inositol
  参考文献：
  名称：

  所有天然存在的磷酸化磷脂酰肌醇的全面，均匀的合成。

  摘要：

  对涉及受体介导的肌醇磷酸酯和磷酸化磷脂酰肌醇的生成的细胞信号转导机制的研究要求容易获得这些天然产物。尽管在过去的十年中已经开发了许多合成方法，但是这些方法中的大多数都存在长度过长和缺乏通用性的问题。在这项工作中，我们描述了所有天然存在的磷脂酰肌醇（例如磷脂酰肌醇，3-磷酸磷脂酰肌醇，4-磷酸酯，5-磷酸酯，3,4-双磷酸酯，3,5-双磷酸酯，4,5-双磷酸酯，和3,4,5-三磷酸酯，具有饱和和不饱和脂肪酸链。

  DOI：

  10.1021/jo0206418

文献信息

• [EN] PHOSPHATIDYLINOSITOL<br/>[FR] PHOSPHATIDYLINOSITOL
  申请人：UNIV ERASMUS MEDICAL CT

  公开号：WO2013081452A1

  公开（公告）日：2013-06-06

  The invention relates to a new pharmaceutical compound, diacyl phosphatdylinositol in which both the sn-1 and the sn-2 place are taken by stearic acid (18:0) (diacyl [18:0; 18:0] phosphatidylinositol), more preferably, wherein said diacyl phosphatidylinositol is compound 1 as depicted in Fig. 10 or a racemate of compounds 1 and 2 as depicted in Fig. 10. Said pharmaceutical compound and pharmaceutical compositions comprising this compound are specifically useful for the treatment of a disease or a condition wherein suppression of T-cell activation is desirable, such as asthma, diabetes Type 1, rheumatoid arthritis, inflammatory bowel disease or psoriasis. Also part of the invention are food items containing the compound(s) of the invention and use thereof in a diet to treat or prevent the disease or condition mentioned above

  该发明涉及一种新的药物化合物，即二酰基磷脂酰肌醇，其中sn-1和sn-2位置均由硬脂酸（18:0）（二酰基[18:0; 18:0]磷脂酰肌醇）占据，更优选地，所述的二酰基磷脂酰肌醇是如图10所示的化合物1，或如图10所示的化合物1和2的拉氏体。所述的药物化合物和包含该化合物的药物组合物特别适用于治疗需要抑制T细胞活化的疾病或病况，如哮喘、糖尿病1型、类风湿性关节炎、炎症性肠病或牛皮癣。该发明的一部分还包括含有该发明化合物的食品以及在饮食中使用它们来治疗或预防上述疾病或病况。
• Design, Synthesis and Biochemical Applications of Analogs of Phosphatidylinositol
  作者：Nanaji Bhamare、Yaping Wang、Ming-Daw Tsai、Karol Bruzik

  DOI：10.1080/10426509608046262

  日期：1996.2.1

  Abstract A general methods for synthesis of diverse precursors of phosphoinositides have been elaborated and applied towards synthesis of a variety of inositol phosphates, phospholipids, and their phosphorothioate, oxygen-labeled and stereoisomeric analogs. The obtained compounds have been used to study mechanism of phosphatidylinositol phospholipase C. The acquired mechanistic information was then applied

  摘要 合成多种磷酸肌醇前体的通用方法已被阐述并应用于合成多种肌醇磷酸酯、磷脂及其硫代磷酸酯、氧标记和立体异构类似物。所得化合物已用于研究磷脂酰肌醇磷脂酶 C 的作用机理。然后将获得的机理信息应用于该酶抑制剂的设计和合成。
• General synthesis of phosphatidylinositol 3-phosphates
  作者：Karol S. Bruzik、Robert J. Kubiak

  DOI：10.1016/0040-4039(95)00317-6

  日期：1995.4

  Uniform synthetic approach to phosphatidylinositol 3-phosphate, 3,4-bisphosphate and 3,4,5-trisphosphate has been elaborated starting from 1D-1-O-tert-butyldiphenylsilyl- and 1,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-myo-inositols using regioselective benzoylation at the 3-, 3,4- and 3,4,5-positions of inositol.

  从1D-1- O-叔丁基二苯基甲硅烷基-和1,6- O-（1,1,3 ，3-四异丙基-1,3-二基） -肌醇-inositols使用区域选择性苯甲酰在3-，3,4-和肌醇3,4,5-位置。
• Regioselective Approach to Phosphatidylinositol 3,5-Bisphosphates: Syntheses of the Native Phospholipid and Biotinylated Short-Chain Derivative
  作者：Regan J. Anderson、Shona L. Osborne、Frederic A. Meunier、Gavin F. Painter

  DOI：10.1021/jo100393c

  日期：2010.6.4

  A selective bis-silylation of 1D-O-TBDPS-myo-inositol leads to a 1,3,5-trisubstituted inositol, which can be advanced to the headgroup of phosphatidylinositol-3,5-bisphosphate [PI(3,5)P-2]. A mild, regioselective method for construction of the diacylglycerol moiety containing differing fatty acid chains, including the naturally occurring lipids, was developed. Their union in the synthesis of the cell-signaling molecule PI(3,5)P-2 containing the RP-I-stearoyl and sn-2-arachidonoyl groups is described. The methodology was also used to generate dioctanoyl-PI(3,5)P-2 and a previously unreported biotin-PI(3,5)P-2 conjugate, which was coupled to neutravidin beads and used to pull down PI(3.5)P-2-binding proteins from the cytosolic extract of adrenal neurosecretory cells. We report the specific pull-down of the PI(3,5)P-2-binding protein svp1p, a known PI(3,5)P-2 effector involved in membrane t To flick
• Regioselective functionalization of unprotected myo-inositol by electrophilic substitution
  作者：Yutaka Watanabe、Tsuyoshi Uemura、Satoe Yamauchi、Kousei Tomita、Takafumi Saeki、Ryousuke Ishida、Minoru Hayashi

  DOI：10.1016/j.tet.2013.03.109

  日期：2013.6

  Unprotected myo-inositol was treated with various electrophiles, such as aroyl chlorides, tosyl chloride and tert-butyldiphenylsilyl chloride in a solution of LiCl/DMA or DMSO to afford regioselectively l,3-di-O-substituted or racemic 1-O-substituted derivatives, depending on a quantity of reagents and reaction time. alpha-Unbranched alkanoic acid anhydrides in LiCl/DMA in the presence of triethylamine were suitable for acylation of myo-inositol, in contrast to the fact that acylation using alkanoyl chlorides in aprotic polar solvents generally does not proceed well due to decomposition of the reagents by the reaction with the solvents. (C) 2013 Elsevier Ltd. All rights reserved.