(±)-2,3:5,6-di-O-isopropylidene-1-O-benzyl-4-O-allyl-myo-inositol | 131146-87-7

• 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: (±)-2,3:5,6-di-O-isopropylidene-1-O-benzyl-4-O-allyl-myo-inositol
• 英文别名: (±)-4-O-allyl-1-O-benzyl-2,3;5,6-di-O-isopropylidene-myo-inositol；(+/-)-6-O-allyl-3-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol
• CAS: 131146-87-7
• 化学式: C₂₂H₃₀O₆
• 分子量: 390.477
• InChiKey: YVRPOJZBKGPTFN-IGOIZDSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (±)-2,3:5,6-di-O-isopropylidene-1-O-benzyl-4-O-allyl-myo-inositol 在 盐酸 、 potassium tert-butylate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.5h， 生成 (+/-)-1,5,6-tri-O-benzyl-4-O-(prop-1-enyl)-myo-inositol
  参考文献：
  名称：

  The synthesis and resolution of (±)-1,5,6-tri-O-benzyl-myo-inositol

  摘要：

  Racemic 1,5,6-tri-O-benzyl-myo-inositol was prepared by five routes and converted into 1,5,6-tri-O-benzyl-2,3-O-isopropylidene-myo-inositol, the camphanates of which were readily separated by chromatography. The absolute configurations of the chiral derivatives were established by their conversion into the known chiral 1,4,5,6-tetra-O-benzyl-myo-inositols. 1D-1,5,6-Tri-O-benzyl-2,3-O-isopropylidene-myo-inositol was converted into 1D-1,3,5,6-tetra-O-benzyl-myo-inositol and thence into 1D-2,4-di-O-methyl-myo-inositol. 1D-1,5,6-Tri-O-benzyl-myo-inositol was converted into 1D-1,2,5,6-tetra-O-benzyl-myo-inositol, the diacetate of which is a chiral analogue of "thermosalient crystals". The potential of the above compounds for the synthesis of natural products is surveyed.

  DOI：

  10.1016/0008-6215(90)80132-m
• 作为产物：
  描述：

  Inositol 在 sodium hydride 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 、 mineral oil 为溶剂， 反应 7.0h， 生成 (±)-2,3:5,6-di-O-isopropylidene-1-O-benzyl-4-O-allyl-myo-inositol
  参考文献：
  名称：

  Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives

  摘要：

  The chemistry and biology of phosphorylated inositols have become intense areas of research during the last two decades due to their involvement in various cellular signaling processes. However, the metabolic instability by phosphatases or kinases and poor penetration make it difficult to become a drug used in the clinic. The bioreversible protection technique can enhance membrane penetration characteristics and increase the stability of phosphorylated inositols against enzymatic degradation and is applied widely in drug discovery and development. In this paper, we described the design and synthesis of 22 bioreversible phosphotriester inositols, along with the initial antitumor activity results. Most compounds exhibited significant cytotoxic activity against human cancer cell lines A549, MDA-MB-231 and HeLa, but lower cellular toxicity on normal cell MCF10A in comparison with Cisplatin. These compounds can be used as probes to study the mechanism of intracellular signal transduction mediated by phosphate inositol or as leads of phosphate inositol drugs in the clinic. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.064

文献信息

• Resolution of Orthogonally Protected <i>myo</i>-Inositols with Novozym 435 Providing an Enantioconvergent Pathway to Ac₂PIM₁
  作者：Alastair M. M. Lee、Gavin F. Painter、Benjamin J. Compton、David S. Larsen

  DOI：10.1021/jo5019188

  日期：2014.11.21

  4-dimethoxyphenyl)benzyl, propyl, and propargyl protection at O-6 in combination with either allyl or benzyl groups at O-3. Bulky protecting groups slow the rate of acetylation. No reaction was observed for 3,6-di-O-triisopropylsilyl-1,2-O-isopropylidene-myo-inositol. The utility of this methodology was demonstrated by the first reported synthesis of an Ac2PIM1 (9), which used both enantiomers of the resolved

  正交保护的手性肌肉肌醇衍生物是更高阶的重要中间体肌醇含肌醇化合物。这里，通过使用固定化酶的Novozym 435以有效地催化5的乙酰化- [R的外消旋1,2-构成的对映体直径：异亚丙基肌醇-inositols在O-3和O-6是化学上和空间上具有多样的保护基团描述。烯丙基，苄基，4-溴-，4-甲氧基-，4-硝基和4-（3,4-二甲氧基苯基）苄基，丙基和炔丙基在O-6的保护下与任何一个烯丙基结合均能成功解决拆分问题或O-3处的苄基。庞大的保护基团会降低乙酰化速度。3,6-di-未观察到反应Ø -triisopropylsilyl -1,2- Ø异亚丙基肌醇肌醇。该方法的实用性通过首次报道的Ac 2 PIM 1（9）合成得到证明，该化合物使用了拆分后的3- O-烯丙基-6- O-苄基-1,2- O-异亚丙基-肌醇的两种对映体。-肌醇的融合合成。