1D-4-O-benzyl-2,3:5,6-di-O-isopropylidene-myo-inositol | 160636-46-4

• 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-4-O-benzyl-2,3:5,6-di-O-isopropylidene-myo-inositol
• CAS: 160636-46-4
• 化学式: C₁₉H₂₆O₆
• 分子量: 350.412
• InChiKey: KWQJPCFJDMBLIR-JNNCMOEMSA-N

物化性质

• 熔点：
  131.5-133.0 °C
• 沸点：
  479.2±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1D-4-O-benzyl-2,3:5,6-di-O-isopropylidene-myo-inositol 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 5.0h， 生成 1D-4-O-benzyl-myo-inositol
  参考文献：
  名称：

  Divergent Synthesis of All Possible Optically Active Regioisomers ofMyo‐Inositol Mono‐ and Bisphosphates

  摘要：

  All possible optically active regioisomers of myo- inositol mono- and bisphosphates were synthesized using inositol derivatives suitably protected with various protecting groups (IR(n)s) as key intermediates. A series of procedures including Novozym 435 catalyzed enzymatic resolution of (3aR, 4S, 7S, 7aR)-rel-3a, 4,7,7a-tetrahydro- 2,2-dimethyl- 1,3- benzodioxole-4,7- diol diacetate, several protection and deprotection reactions, and acyl migration afforded two enantiomeric pairs of IR5 and six enantiomeric pairs of IR4. Phosphorylation of these key intermediates by the phosphitylation and oxidation procedure gave the target products after removal of the protecting groups.[GRAPHICS]

  DOI：

  10.1080/07328300701540225
• 作为产物：
  描述：

  (3aS,4R,7R,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-4,7-bis(phenylmethoxy)-1,3-benzodioxole 在 palladium on activated charcoal 、 四氧化锇 N-甲基吲哚酮 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 85.0h， 生成 1D-4-O-benzyl-2,3:5,6-di-O-isopropylidene-myo-inositol
  参考文献：
  名称：

  Divergent Synthesis of All Possible Optically Active Regioisomers ofMyo‐Inositol Mono‐ and Bisphosphates

  摘要：

  All possible optically active regioisomers of myo- inositol mono- and bisphosphates were synthesized using inositol derivatives suitably protected with various protecting groups (IR(n)s) as key intermediates. A series of procedures including Novozym 435 catalyzed enzymatic resolution of (3aR, 4S, 7S, 7aR)-rel-3a, 4,7,7a-tetrahydro- 2,2-dimethyl- 1,3- benzodioxole-4,7- diol diacetate, several protection and deprotection reactions, and acyl migration afforded two enantiomeric pairs of IR5 and six enantiomeric pairs of IR4. Phosphorylation of these key intermediates by the phosphitylation and oxidation procedure gave the target products after removal of the protecting groups.[GRAPHICS]

  DOI：

  10.1080/07328300701540225

文献信息

• The synthesis and resolution of (±)-1,4-diO-benzyl-2,3-O-isopropylidene-myo-inositol
  作者：Trupti Desai、Jill Gigg、Roy Gigg、Eloísa Martín-Zamora、Nathalie Schnetz

  DOI：10.1016/0008-6215(94)84081-4

  日期：1994.5

  Abstract An improved procedure for the preparation of 1,2-O-isopropylidene-myo-inositol is described. Racemic 1,4-di-O-benzyl-2,3-O-isopropylidene-myo-inositol was prepared by tinmediated benzylation of 1,2-O-isopropylidene-myo-inositol and resolved readily by crystallisation of the ω-camphanates. The use of the chiral 1,4-di-O-benzyl-2,3-O-isopropylidene-myo-inositols as intermediates for the preparation

  摘要描述了一种制备1,2-O-异亚丙基-肌醇的改进方法。外消旋的1，4-二-O-苄基-2，3-O-异亚丙基-肌醇通过锡介导的1，2-O-异亚丙基-肌醇的苄基化制备，并容易通过ω-樟脑酸酯的结晶而拆分。研究了手性1,4-二-O-苄基-2,3-O-异亚丙基-肌醇的中间体作为制备肌醇其他手性衍生物的中间体。
• US7589072B2
  申请人：——

  公开号：US7589072B2

  公开（公告）日：2009-09-15