(+)-3,4-di-O-allyl-5,6-di-O-benzyl-myo-inositol | 116786-69-7

• 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: (+)-3,4-di-O-allyl-5,6-di-O-benzyl-myo-inositol
• CAS: 116786-69-7
• 化学式: C₂₆H₃₂O₆
• 分子量: 440.536
• InChiKey: WAFNMECKFDMVMZ-XCQFYCGYSA-N

物化性质

• 沸点：
  563.1±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  32.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (+)-3,4-di-O-allyl-5,6-di-O-benzyl-myo-inositol 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 四丁基溴化铵 、 二正丁基氧化锡 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 51.0h， 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：

  (+/-)-1,6-di-O-allyl-2,3:4,5-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 4.5h， 生成 (+)-3,4-di-O-allyl-5,6-di-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

文献信息

• A novel reagent for the synthesis of -inositol phosphates: ,-diisopropyl dibenzyl phosphoramidite
  作者：Kuo-Long Yu、Bert Fraser-Reid

  DOI：10.1016/0040-4039(88)85313-9

  日期：1988.1

  found that partially protected inositols are phosphorylated in near quantitative yields by use of ,-diisopropyl dibenzyl phosphoramidite, 1-H-tetrazole and MCPBA in CH2Cl2. Subsequent hydrogenolysis of the resulting perbenzylated products gives the corresponding free inositol phosphates in quantitative yields without tedious ion exchange chromatography.

  已经发现，部分保护的肌醇在接近定量的产率通过使用磷酸，二异丙基亚磷酰胺二苄基，1- ħ四唑和MCPBA在CH 2氯2。随后的所得过苄基化产物的氢解反应以定量收率得到相应的游离肌醇磷酸酯，而无需乏味的离子交换色谱。
• An efficient chemoenzymic access to optically active myo-inositol polyphosphates
  作者：Da-Ming Gou、Yeuk-Chuen Liu、Ching-Shih Chen

  DOI：10.1016/0008-6215(92)85038-2

  日期：1992.10

  Abstract The 1,4,5-tris-, 1,3,4-tris-, and 1,3,4,5-tetrakis-phosphates of 1 d -myo-inositol have been prepared in their enantiomerically pure forms from the two enantiomers of 1,2:5,6-di-O-cyclohexylidene-myo-inositol. A facile enzymic preparation is also described of these chiral intermediates through enantiospecific deacylation of the corresponding racemic esters.

  摘要从两种对映体中以对映体纯的形式制备了1 d-肌醇的1,4,5-tris-，1,3,4-tris-和1,3,4,5-四-磷酸1,2：5,6-二-O-环己叉基-肌醇的对映体。还描述了通过手性中间体通过相应外消旋酯的对映特异性脱酰作用的简便酶制剂。
• An efficient route toD-myo-inositol 1,3,4-triphosphate andD-myo-inositol 1,3,4,5-tetrakisphosphate
  作者：Da-Ming Gou、Ching-Shih Chen

  DOI：10.1016/s0040-4039(00)77699-4

  日期：1992.2

  Multigram quantities of the title compounds in their enantiomerically-pure forms have been prepared by employing a chiral precursor which can be obtained via a facile enzymatic process.
• Synthesis of the D-3 Series of Phosphatidylinositol Phosphates
  作者：Da-Sheng Wang、Ching-Shih Chen

  DOI：10.1021/jo960602u

  日期：1996.1.1

  The 3-mono-, 3,4-bis-, and 3,4,5-trisphosphates of L-alpha-phosphatidyl-D-myo-inositol have been synthesized in their optically active forms from the two enantiomers of 1,2:5,6-di-O-cyclohexylidenemyo-inositol. These chiral precursors were prepared by a facile biocatalytic resolution, in which the 8-butyryl ester of the racemic compound was subjected to enantioselective hydrolysis by porcine pancreatic lipase in a biphasic system. The overall yield from individual chiral precursors ranged from 32% for the 3,4,5-trisphosphate to 39% for the monophosphate.