(3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol | 371155-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol
• 英文别名: (+)-(1S,2R,3R,4S)-2,3-O-isopropylidenecyclohex-5-ene-1,2,3,4-tetrol；(3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-2,3-benzodioxole-4,7-diol；(3aR,4S,7S,7aR)-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxole-4,7-diol
• CAS: 371155-65-6
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: BJOPOVQRPOSWLW-RULNZFCNSA-N

物化性质

• 沸点：
  356.5±42.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol 在 palladium on activated charcoal 、 四氧化锇 N-甲基吲哚酮 、 氢气 、 四丁基碘化铵 、 sodium hydride 、 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 (D)-1,2:4,5-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
• 作为产物：
  描述：

  1-((4S,5S)-5-Acryloyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propenone 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol
  参考文献：
  名称：

  通过闭环易位立体选择性合成肌醇：糖基磷脂酰肌醇（GPI）锚合成的基础。

  摘要：

  在这里我们报告通过闭环易位的肌肉肌醇的简洁立体选择性合成。易得的D-酒石酸双-Weinreb酰胺用作关键中间体。[反应：看文字]

  DOI：

  10.1021/ol025680k

文献信息

• Facile Syntheses of All Possible Diastereomers of Conduritol and Various Derivatives of Inositol Stereoisomers in High Enantiopurity from <i>m</i><i>yo</i>-Inositol
  作者：Yong-Uk Kwon、Changgook Lee、Sung-Kee Chung

  DOI：10.1021/jo016237a

  日期：2002.5.1

  Inositol phosphate analogues have been useful in probing the structure-activity relationships between inositol phosphates and biomacromolecules, and in studying biological functions of newly found inositol phosphates. Thus, a systematic and ready access to inositol stereoisomers is highly desirable. And practical and convenient syntheses of conduritols and related compounds are also important because of their

  基于磷酸肌醇的信号传导过程在细胞内信号转导事件中至关重要。肌醇磷酸酯类似物可用于探测肌醇磷酸酯和生物大分子之间的构效关系，并用于研究新发现的肌醇磷酸酯的生物学功能。因此，非常需要系统且容易获得肌醇立体异构体。由于其生物活性及其在制备其他生物活性分子中的合成效用，因此，实用和方便的合成方法是重要的。我们在此报告了从肌醇中高对映体纯度的所有可能的conduritol非对映异构体和8种肌醇立体异构体的各种衍生物的合成，
• Synthesis of three enantiomeric pairs of scyllo-Inositol phosphate and molecular interactions between all possible regioisomers of scyllo-Inositol phosphate and inositol 1,4,5-Trisphosphate 3-Kinase
  作者：Yong-Uk Kwon、Jungkyun Im、Gildon Choi、Young-Soo Kim、Kwan Yong Choi、Sung-Kee Chung

  DOI：10.1016/s0960-894x(03)00629-2

  日期：2003.9

  scyllo-Inositol phosphates, which are among the stereoisomers of myo-inositol phosphate, can have 15 possible regioisomers including three enantiomeric pairs: scyllo-I(1,2)P(2), scyllo-I(1,2,4)P(3), scyllo-I(1,2,3,4)P(4). We herein describe the facile synthetic routes to the three enantiomeric pairs of scyllo-inositol phosphate and the molecular interactions between 15 regioisomers of scyllo-inositol

  肌醇磷酸的立体异构体中的鞘氨醇磷酸酯可具有15种可能的区域异构体，包括三个对映异构体对：鞘脂-I（1,2）P（2），鞘脂-I（1,2,4）P （3），scyllo-I（1,2,3,4）P（4）。我们在本文中描述了三个磷酸肌醇磷酸对映体对的简便合成路线，以及磷酸肌醇磷酸肌醇和肌醇1,4,5-三磷酸3-激酶的15个区域异构体之间的分子相互作用。讨论了酶结合位点的几何形状。
• Facile Synthetic Routes to All Possible Enantiomeric Pairs of Conduritol Stereoisomers via Efficient Enzymatic Resolution of Conduritol B and C Derivatives
  作者：Yong-Uk Kwon、Sung-Kee Chung

  DOI：10.1021/ol0164233

  日期：2001.9.1

  The first synthesis of all possible enantiomeric pairs of conduritol stereoisomers has been accomplished by efficient enzymatic resolution of conduritol B and C derivatives, followed by oxidation/reduction and the Mitsunobu reaction in stereo- and regioselective manners. Reaction: see text.
• Divergent Synthesis of All Possible Optically Active Regioisomers of<i>Myo‐</i>Inositol Mono‐ and Bisphosphates
  作者：Kyung‐Chang Seo、Seok‐Ho Yu、Sung‐Kee Chung

  DOI：10.1080/07328300701540225

  日期：2007.9

  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]
• Stereoselective Synthesis of <i>myo</i>-Inositol via Ring-Closing Metathesis:  A Building Block for Glycosylphosphatidylinositol (GPI) Anchor Synthesis
  作者：Rosemary M. Conrad、Michael J. Grogan、Carolyn R. Bertozzi

  DOI：10.1021/ol025680k

  日期：2002.4.1

  Here we report a concise stereoselective synthesis of myo-inositol via ring-closing metathesis. A readily available bis-Weinreb amide of D-tartrate served as a key intermediate. [reaction: see text]

  在这里我们报告通过闭环易位的肌肉肌醇的简洁立体选择性合成。易得的D-酒石酸双-Weinreb酰胺用作关键中间体。[反应：看文字]