(-)-1D-1,4,5-tris-O-allyl-2,3,6-tris-O-benzyl-myo-inositol | 98925-54-3

• 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: (-)-1D-1,4,5-tris-O-allyl-2,3,6-tris-O-benzyl-myo-inositol
• 英文别名: (+)-1,3,4-tri-O-allyl-2,5,6-tri-O-benzyl-myo-inositol；(±)-2,3,6-tri-O-benzyl-1,4,5-tri-O-allyl-myo-inositol；(+/-)-1,4,5-tri-O-allyl-2,3,6-tri-O-benzyl-myo-inositol；1,4,5-tri-O-allyl-2,3,6-tri-O-benzyl-myo-inositol
• CAS: 98925-54-3；104873-75-8；111466-06-9；114418-97-2；140148-52-3
• 化学式: C₃₆H₄₂O₆
• 分子量: 570.726
• InChiKey: ODPDGVXEMDSAFL-KPTSLFCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.47
• 重原子数：
  42.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (-)-1D-1,4,5-tris-O-allyl-2,3,6-tris-O-benzyl-myo-inositol 在 palladium on activated charcoal 对甲苯磺酸 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 6.0h， 生成 (+/-)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol
  参考文献：
  名称：

  Gigg, Jill; Gigg, Roy; Payne, Sheila, Journal of the Chemical Society. Perkin transactions I, 1987, p. 423 - 430

  摘要：

  DOI：
• 作为产物：
  描述：

  (±)-1,4-di-O-allyl-2,3:5,6-di-O-isopropylidene-myo-inositol 在 盐酸 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 32.0h， 生成 (-)-1D-1,4,5-tris-O-allyl-2,3,6-tris-O-benzyl-myo-inositol
  参考文献：
  名称：

  Gigg, Jill; Gigg, Roy; Payne, Sheila, Journal of the Chemical Society. Perkin transactions I, 1987, p. 423 - 430

  摘要：

  DOI：

文献信息

• The preparation of racemic and enantiomerically pure myo-inositol derivatives as intermediates for the synthesis of phosphatidylinositol 3-, 3,4-bis-, and 3,4,5-tris-phosphates and for the synthesis of analogues of 1d-myo-inositol 1,3,4,5-tetrakisphosphate
  作者：Trupti Desai、Jill Gigg、Roy Gigg、Eloisa Martín-Zamora

  DOI：10.1016/s0008-6215(96)00211-x

  日期：1996.12

  1,5,6-tris(dibenzyl phosphate) and (±)-2,4-di-O-benzyl-1,5,6-tri-O-p-methoxybenzyl-myo-inositol (intermediates for phosphatidylinositol 3,4,5-trisphosphate). Some of the intermediates used in the above preparations were also used for the synthesis of myo-inositol derivatives suitable for the preparation of analogues of 1d-myo-inositol 1,3,4,5-tetrakisphosphate. Thus 1l-2,4-di-O-benzyl-5-O-p-methoxybenzyl-myo-inositol

  摘要这里提供了先前在初步通报中描述的通过1,2-O-异亚丙基-肌醇的锡介导的烯丙基化和苄基化反应获得的产品的详细信息。这些反应的一些产物，特别是3,4,6-三-O-烯丙基-和3,5,6-三-O-烯丙基-1，2-O-异亚丙基-肌醇，已被用于制备中间体，用于合成标题化合物。描述了以下化合物的合成：1l-2,4,5,6-四-O-苄基-1-Op-甲氧基苄基-肌醇（磷脂酰肌醇3-磷酸酯的中间体），1l-2,4,5 -三-O-苄基-肌醇1,6-双（磷酸二苄酯）和1l-2,4,5-三-O-苄基-1,6-二-Op-甲氧基苄基-肌醇（中间体磷脂酰肌醇3,4-二磷酸），1l-2,4-二-O-苄基-肌醇1,5,6-三（磷酸二苄基）和（±）-2,4-二-O-苄基-1 ，5,6-三-对-甲氧基苄基-肌醇（磷脂酰肌醇3,4,5-三磷酸酯的中间体）。在上述制剂中使用的一些中间体也用于合成肌醇衍生物，其适合于制备1d-肌醇1
• Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives
  作者：Wenbin Chen、Zhaohui Deng、Kuangyu Chen、Daolei Dou、Fanbo Song、Luyuan Li、Zhen Xi

  DOI：10.1016/j.ejmech.2015.01.064

  日期：2015.3

  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.
• Synthesis of (±)-1,2,4-tri-O-benzyl-myo-inositol
  作者：Jill Gigg、Roy Gigg、Sheila Payne、Robert Conant

  DOI：10.1016/0008-6215(85)85064-3

  日期：1985.7
• The alkylation of dibutylstannylene derivatives of 1,2-O-isopropylidene-myo-inositol.
  作者：Jill Gigg、Roy Gigg、Eloisa Martin-Zamora

  DOI：10.1016/s0040-4039(00)73573-8

  日期：1993.4

  Benzylation (or allylation) of 1,2-O-isopropylidene-myo-inositol in the presence of an excess of dibutyltin oxide gives, as major products, the readily isolable 3,4,6- (12) and 3,5,6-tri-O-alkyl (13) derivatives which are valuable intermediates for the synthesis of inositol phosphates of the phosphatidylinositol cycle.