4-O-benzyl-myo-inositol 1,3,5-orthoformate | 120268-33-9

• 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: 4-O-benzyl-myo-inositol 1,3,5-orthoformate
• 英文别名: 9-Phenylmethoxy-2,4,10-trioxatricyclo[3.3.1.13,7]decane-6,8-diol
• CAS: 120268-33-9
• 化学式: C₁₄H₁₆O₆
• 分子量: 280.277
• InChiKey: ZMBYIYSHPAMJOY-UHFFFAOYSA-N

物化性质

• 沸点：
  478.8±45.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-O-benzyl-myo-inositol 1,3,5-orthoformate 在 sodium tetrahydroborate 、 草酰氯 、 四丁基氢氧化铵 、 sodium hydride 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.41h， 生成 4,4',6-tri-O-benzyl-2-O-methoxymethyl-4-C-hydroxymethyl-myo-inositol 1,3,5-orthoformate
  参考文献：
  名称：

  的（±）-Tetrodotoxin从新颖的和立体控制合成米哟肌醇

  摘要：

  描述了由肌醇合成（±）-河豚毒素的新颖且立体控制的合成。关键步骤包括将羟基逐步氧化为羰基官能团，然后加入特定的亲核试剂，包括连续的螺α-氯环氧化物的形成以及其与叠氮化物阴离子的开环，以得到所需的支链结构（5 → 6，17 → 18 → 19 → 20和23 → 24 → 25），在高产率的所需区域选择性和立体选择性。α-叠氮醛25逐步转化为δ-内酯29然后还原叠氮化物，引入胍基部分，醛形成和脱保护，产生了（±）-河豚毒素。

  DOI：

  10.1021/jo050342t
• 作为产物：
  描述：

  (1α,5α,6β,7α,8β,9α)-8-(benzyloxy)-9-(tertbutyldimethylsiloxy)-2,4,10-trioxaadamantan-6-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 4-O-benzyl-myo-inositol 1,3,5-orthoformate
  参考文献：
  名称：

  1D-和1L-肌醇1,3,4,5，-四磷酸的合成

  摘要：

  1D-和1L-的合成肌肉肌醇1,3,4,5，-tetraphosphate（1A和1B RESP）进行说明。二苯甲基化的肌醇9a和9b通过磷酸化分别通过两种途径制备，分别得到1a和1b。一方面，从肌醇得到的外消旋体3a / 3b通过转化为非对映异构氨基甲酸酯5a和5b而分解。5a和5b的苯甲酰化和脱保护子得到对映异构体9a和9b分别。另一方面，用猪肝酯酶处理二酯18可得到具有高对映体过量的酯21a。21a的苯甲酰化和脱保护得到9b。使用相同的酶水解，然后进行保护-脱保护序列，得到二苄基衍生物9a。

  DOI：

  10.1002/hlca.19880710548

文献信息

• Chelation controlled regiospecific O-substitution of myo-inositol orthoesters: convenient access to orthogonally protected myo-inositol derivatives
  作者：Subramanian Devaraj、Mysore S. Shashidhar、Shailesh S. Dixit

  DOI：10.1016/j.tet.2004.11.025

  日期：2005.1

  protection of the three secondary hydroxyl groups of orthoester derivatives of myo-inositol, utilizing the subtle differences in reactivity exhibited by its alkali metal alkoxides due to differences in their ability to form chelates, is described. This method provides convenient access to orthogonally protected myo-inositol derivatives. A comparison of the methylation of racemic 4-O-trityl-myo-inositol

  描述了一种完全区域选择性保护肌醇原酸酯衍生物的三个仲羟基的通用方法，该方法利用其碱金属醇盐由于形成螯合物的能力不同而表现出的反应性的细微差异。该方法提供了对正交保护的肌醇衍生物的方便访问。比较外消旋 4-O-三苯甲基-肌醇 1,3,5-原甲酸在钠离子或锂离子存在下的甲基化表明，通过与锂螯合的 C4-醇盐的稳定性克服了 C6 提供的空间位阻-轴取代基决定亲核O-取代过程中的区域选择性。
• Inositol compounds and uses of same in the treatment of diseases characterized by abnormal protein folding or aggregation or amyloid formation, desposition, accumulation or persistence
  申请人：Cruz Antonio

  公开号：US20070111970A1

  公开（公告）日：2007-05-17

  Inositol derivatives are described that are represented by the structural formula I wherein X is a radical of scyllo-inositol wherein one or more of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are independently alkyl, alkenyl, alkynyl, alkylene, alkenylene, alkoxy, alkenyloxy, cycloalkyl, cycloalkenyl, cycloalkoxy, aryl, aryloxy, arylalkoxy, aroyl, heteroaryl, heterocyclic, acyl, acyloxy, sulfoxide, sulfate, sulfonyl, sulfenyl, sulfonate, sulfinyl, amino, imino, azido, thiol, thioalkyl, thioalkoxy, thioaryl, nitro, cyano, halo, seleno, silyl, silyloxy, silylthio, carboxyl, carbonyl, carbamoyl, or carboxamide and the other of R 1 , R 2 , R 3 , R 4 , R 5 , or R 6 are hydroxyl, or pharmaceutically acceptable salts thereof. The compounds, compositions comprising same and methods using same are described for use in the prevention and/or treatment of diseases characterized by abnormal protein folding or aggregation or amyloid formation, desposition, accumulation or persistence.
• SCYLLO-INOSITOL DERIVATIVES AND THEIR USE IN THE TREATMENT OF DISEASES CHARACTERIZED BY ABNORMAL PROTEIN FOLDING OR AGGREGATION OR AMYLOID FORMATION, DEPOSITION, ACCUMULATION OR PERSISTENCE
  申请人：Cruz Antonio

  公开号：US20090170957A1

  公开（公告）日：2009-07-02

  Scyllo-Inositol derivatives represented by structural formula II are described, wherein at least one and not more than five of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is hydroxyl and the other of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently alkyl, alkenyl, alkynyl, alkylene, alkenylene, alkoxy, alkenyloxy, cycloalkyl, cycloalkenyl, cycloalkoxy, aryl, aryloxy, arylalkoxy, aroyl, heteroaryl, heterocyclic, acyl, acyloxy, sulfoxide, sulfate, sulfonyl, sulfenyl, sulfonate, sulfinyl, ammo, lmmo, azido, thiol, thioalkyl, thioaryl, mtro, cyano, halo, seleno, silyl, silyloxy, silylthio, carboxyl, carbonyl, carbamoyl or carbamide, or pharmaceutically acceptable salts thereof. Said derivatives and compositions comprising the same are useful in the prevention and/or treatment of diseases characterized by abnormal protein folding or aggregation or amyloid formation, deposition, accumulation or persistence.
• Inositol Compounds and Uses of Same in the Treatment of Diseases Characterized by Abnormal Protein Folding or Aggregation or Amyloid Formation, Desposition, Accumulation or Persistence
  申请人：Curz Antonio

  公开号：US20100105631A1

  公开（公告）日：2010-04-29

  Inositol derivatives are described that are represented by the structural formula I wherein X is a radical of scyllo-inositol wherein one or more of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are independently alkyl, alkenyl, alkynyl, alkylene, alkenylene, alkoxy, alkenyloxy, cycloalkyl, cycloalkenyl, cycloalkoxy, aryl, aryloxy, arylalkoxy, aroyl, heteroaryl, heterocyclic, acyl, acyloxy, sulfoxide, sulfate, sulfonyl, sulfenyl, sulfonate, sulfinyl, amino, imino, azido, thiol, thioalkyl, thioalkoxy, thioaryl, nitro, cyano, halo, seleno, silyl, silyloxy, silylthio, carboxyl, carbonyl, carbamoyl, or carboxamide and the other of R 1 , R 2 , R 3 , R 4 , R 5 , or R 6 are hydroxyl, or pharmaceutically acceptable salts thereof. The compounds, compositions comprising same and methods using same are described for use in the prevention and/or treatment of diseases characterized by abnormal protein folding or aggregation or amyloid formation, desposition, accumulation or persistence.
• SCREENING METHODS FOR AMYLOID BETA MODULATORS
  申请人：Slon-Usakiewicz Jacek

  公开号：US20110028719A1

  公开（公告）日：2011-02-03

  The present invention relates to methods for screening, identifying, and/or quantifying modulators of amyloid and/or aggregates, fibrils or components thereof, in particular modulators of amyloid β-peptide (Aβ) or Aβ fibrils. Aspects of the invention provide methods for screening putative modulators against an Amyloid target, in particular an Aβ target, so as to determine which modulators bind to or interact with the target, or interfere with the interaction of an indicator agent and the target. Particular aspects of the invention employ mass spectrometric methods for the screening of an Amyloid target against compound libraries, in particular mixtures of compounds or combinatorial libraries.