(+)-conduritol E | 139559-64-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-conduritol E
• 英文别名: Conduritol E；(1S,2S,3S,4S)-cyclohex-5-ene-1,2,3,4-tetrol
• CAS: 139559-64-1
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: LRUBQXAKGXQBHA-BXKVDMCESA-N

物化性质

• 熔点：
  65 °C(Solv: hexane (110-54-3); ethyl ether (60-29-7))
• 沸点：
  281.9±40.0 °C(Predicted)
• 密度：
  1.666±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-conduritol E 在 palladium on activated charcoal 、 水 作用下， 生成 [1S-(1α,2α,3β,4β)]-cyclohexane-1,2,3,4-tetrol
  参考文献：
  名称：

  69.环糖醇。第八部分 碘离子消除邻近的磺酰氧基

  摘要：

  DOI：

  10.1039/jr9580000375
• 作为产物：
  描述：

  cis-1,2-dihydrocatechol 在 吡啶 、 ammonium hydroxide 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (+)-conduritol E
  参考文献：
  名称：

  An efficient enzymatic preparation of (+)- and (−)-conduritol E, a cyclitol with C2 symmetry

  摘要：

  Lypozyme(R) IM (immobilised lipase from Mucor miehei) catalyses the enantiomeric alcoholysis of tetraacetylconduritol E (+/-)-2 to give enantiopure (1R,2R,3R,4R)-tetrahydroxycyclohex-5-ene (-)-1, and the unreacted ester (1S,2S,3S,4S)-tetraacetyloxycyclohex-5-ene, (+)-2. The latter was transformed by basic hydrolysis into (+)-1 in high yield and 95% ee. Selective amination of partial ester (-)-3, obtained by short alcoholysis of (+/-)-2, furnished the previously unreported conduramine F-4, (-)-4. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00129-8

文献信息

• Halichondrin B:  Synthesis of the C1−C22 Subunit
  作者：William T. Lambert、Gregory H. Hanson、Farid Benayoud、Steven D. Burke

  DOI：10.1021/jo051479m

  日期：2005.11.1

  steps and 4% overall yield. In a separate route, 7 was also synthesized in 18 steps and 2% overall yield from a derivative of α-d-glucoheptonic acid γ-lactone (62). While the former route installs the fully elaborated C-ring endowed with the correct C12 stereochemistry early in the synthesis, the latter features a late-stage introduction of the C12 stereocenter during the ultimate one-pot Michael addition/ketalization

  描述了两种到蛇绿蛋白B C1-C22亚基的有效途径。笼式缩酮7由18个步骤由（+）-conduritol E（27）组装而成，其中包含11个嵌入ABCDEF环框架内的不对称中心，总产率为4％。在单独的路线中，还通过18个步骤合成了7种化合物，由α - d-葡萄糖庚酸γ-内酯的衍生物合成的总收率为2％（62）。前一种方法在合成初期就安装了完全精巧的C环，并具有正确的C12立体化学，而后者则采用了在最终的一锅迈克尔加成/缩酮化级联反应中后期引入C12立体中心以形成CDE-的方法。笼的环形系统。通过比较这两种策略，讨论了C12立体中心对于关键缩酮化事件的重要性。
• A unified and common intermediate strategy for the asymmetric total synthesis of 3-deoxy-neo-inositol and conduritol E
  作者：Amarendra Panda、Rayhan Gafur Biswas、Shantanu Pal

  DOI：10.1016/j.tetlet.2016.06.127

  日期：2016.8

  3-deoxy-neo-inositol and conduritol E starting from d-ribose via a common chiral cyclohexenol derivative. The focal attributes of the synthetic route include stereoselective Grignard reaction, Wittig olefination, ring closing metathesis (RCM), and cis dihydroxylation.

  对于对映体纯的3-脱氧-新肌醇和conduritol E，从d-核糖开始，通过常见的手性环己烯醇衍生物，已经概述了一种有效，简单且统一的合成方法。合成路线的重点属性包括立体选择性格氏反应，Wittig烯烃化，闭环复分解（RCM）和顺式二羟基化。
• 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，
• Halichondrin B:  Synthesis of a C1−C14 Model via Desymmetrization of (+)-Conduritol E
  作者：William T. Lambert、Steven D. Burke

  DOI：10.1021/ol027389a

  日期：2003.2.1

  [reaction: see text] A model C1-C14 segment (1) of halichondrin B was synthesized from (+)-conduritol E (7) in 18 steps and 2.9% overall yield. Key features of the synthesis include the novel ozonolytic desymmetrization of C(2)-symmetric diol 6, the early-stage construction of the C-ring which accompanies installation of the crucial C12 stereocenter, and the use of an enol ether C14-ketone surrogate

  [反应：参见正文]由（+）-松节油醇E（7）以18个步骤合成halichondrin B的模型C1-C14片段（1），总产率为2.9％。合成的关键特征包括C（2）-对称二醇6的新型臭氧分解脱对称，关键C12立体中心的安装过程中C环的早期构建以及烯醇醚C14-酮替代物的使用作为CDE“笼养”缩酮的前身。
• Desymmetrization of Cyclohexadienylsilanes. Regio-, Diastereo-, and Enantioselective Access to Sugar Mimics
  作者：Rémy Angelaud、Odile Babot、Trevor Charvat、Yannick Landais

  DOI：10.1021/jo991225z

  日期：1999.12.1

  Desymmetrization of cyclohexadienylsilanes available from Birch reduction of the corresponding arylsilanes is efficiently carried out using Sharpless asymmetric dihydroxylation and aminohydroxylation. Complete diastereocontrol and reasonable enantiocontrol have been attained during the preparation of the desired diols. An excellent regiocontrol has also been observed during aminohydroxylation of dienylsilanol 6b. The resulting diol 8 and hydroxycarbamate 27 have then been elaborated further, offering a straightforward access to various types of cyclitols, aminocyclitols, carbasugars, as well as the antibiotic palitantine 4. The complete functionalization of the original arylsilanes 5 is thus typically achieved in fewer than eight steps with high stereoselectivities and excellent overall yield.