(1R,3R,4R,6S)-4,5,6-三(苯基甲氧基)环己烷-1,2,3-三醇 | 131233-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1R,3R,4R,6S)-4,5,6-三(苯基甲氧基)环己烷-1,2,3-三醇
• 英文名称: 3,4,5-tri-O-benzyl myo-inositol
• 英文别名: (+/-)-1,5,6-tri-O-benzyl-myo-inositol；1,5,6-Tobmi；(1R,3R,4R,6S)-4,5,6-tris(phenylmethoxy)cyclohexane-1,2,3-triol
• CAS: 131233-70-0
• 化学式: C₂₇H₃₀O₆
• 分子量: 450.532
• InChiKey: DLTULJLWMBPREM-UZXVYOLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,3R,4R,6S)-4,5,6-三(苯基甲氧基)环己烷-1,2,3-三醇 在 吡啶 、 sodium hydroxide 、 四丁基溴化铵 、 二正丁基氧化锡 作用下， 以 甲醇 为溶剂， 反应 36.0h， 生成 1,2,5,6-tetra-O-benzyl-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：

  (+/-)-4-O-allyl-1,5,6-tri-O-benzyl-myo-inositol 在 palladium on activated charcoal 作用下， 生成 (1R,3R,4R,6S)-4,5,6-三(苯基甲氧基)环己烷-1,2,3-三醇
  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

文献信息

• Application of the Arbuzov reaction for the synthesis of phosphonate analogues of myo-inositol 1,2-bis- and 1,2,6-trisphosphates and methyl α-D-mannopyranoside 2,3,4-trisphosphate
  作者：Grzegorz Salamoríczyk、Nicola Rehnberg、Bożena Krawiecka、Jan Michalski

  DOI：10.1016/s0040-4039(96)02382-9

  日期：1997.1

  6-tris-phosphites with benzyl bromoacetate, followed by catalytic () hydrogenolysis affords (±)-myo-inositol 1,2-bis- and 1,2,6-tris(carboxymethylphosphonate). The same procedure is used for the synthesis methyl α-D-mannopyranoside 2,3,4-tris(carboxymethylphosphonate).

  - perbenzylated（±）的反应肌醇肌醇1,2-双-和1,2,6-三-亚磷酸酯用溴乙酸苄酯，接着通过催化（）氢解，得到（±） -肌醇肌醇1,2-双-和1,2,6-三（羧甲基膦酸酯）。合成α-D-甘露吡喃糖苷2,3,4-三（羧甲基膦酸酯）的步骤相同。
• Derivatives of cyclohexane
  申请人：Perstorp AB

  公开号：US05278332A1

  公开（公告）日：1994-01-11

  New derivatives of cyclohexane in substantially pure form suitable as pharmaceutical, foodstuff or as a stabilizer.

  新型环己烷衍生物以实质纯形式存在，适用于制药、食品或稳定剂。