(1S,2R,3R,4S)-1,4-di-O-benzylconduritol B | 391201-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R,3R,4S)-1,4-di-O-benzylconduritol B
• 英文别名: 1,4-di-O-benzylconduritol B；4-Cyclohexene-1,2-diol, 3,6-bis(phenylmethoxy)-, (1S,2S,3S,6S)-；(1S,2S,3S,6S)-3,6-bis(phenylmethoxy)cyclohex-4-ene-1,2-diol
• CAS: 391201-70-0
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: HEAOJLZDFTYKHK-VNTMZGSJSA-N

物化性质

• 沸点：
  484.8±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  (1S,2R,3R,4S)-1,4-di-O-benzylconduritol B 在 palladium on activated charcoal 吡啶 、 四氮唑 、 ruthenium trichloride 、 sodium periodate 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 56.17h， 生成 (+/-)-myo-Inositol-1-phosphate
  参考文献：
  名称：

  肌醇磷酸酯的灵活立体和区域选择性合成（第 1 部分）：通过对称 Conduritol B 衍生物

  摘要：

  描述了用于制备肌醇磷酸酯的实用路线。通过酶促拆分二乙酰氧基硬糖醇关键中间体，可以从对苯醌制备两种形式的光学纯化合物。单取代的肌醇衍生物可以通过破坏 conduritol B 衍生物的 C2 对称性来获得。通过将先前报道的对称方法与这种新的非对称方法相结合，可以合成多种肌醇磷酸酯。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  DOI：

  10.1002/ejoc.200400911
• 作为产物：
  描述：

  (+)-(1R,2S,3S,4R)-2,3-dibromocyclohex-5-ene-1,4-diol 、 苯甲醇钠 以 苯甲醇 为溶剂， 以47%的产率得到(1S,2R,3R,4S)-1,4-di-O-benzylconduritol B
  参考文献：
  名称：

  Regiospecific phosphohydrolases from Dictyostelium as tools for the chemoenzymatic synthesis of the enantiomers d-myo-inositol 1,2,4-trisphosphate and d-myo-inositol 2,3,6-trisphosphate: non-physiological, potential analogues of biologically active d-myo-inositol 1,3,4-trisphosphate

  摘要：

  A new de novo synthesis of the enantiomeric pair D-myo-inositol 1,2,4-trisphosphate and D-myo-inositol 2,3,6-trisphosphate is described. Starting from enantiopure dibromocyclohexenediol, several C-2 Symmetrical building blocks were synthesized which gave access to D-myo-inositol 1,2,4,5-tetrakisphosphate and D-Myo-inositol 1,2,3,6-tetrakisphosphate. Exploiting the high regiospecificity of two partially purified phosphohydrolases from Dictyostelium, a 5-phosphatase and a phytase, the inositol tetrakisphosphates were converted enzymatically to the target compounds. Their potential to modulate the activity of Ins(3,4,5,6)P-4 I-kinase was investigated and compared with the effects Of D-myo-inositol 1,3,4-trisphosphate. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00536-4

文献信息

• Stereoselective Synthesis of myo-, neo-, L-chiro, D-chiro, allo-, scyllo-, and epi-Inositol Systems via Conduritols Prepared from p-Benzoquinone
  作者：Michael Podeschwa、Oliver Plettenburg、Jochen vom Brocke、Oliver Block、Stephan Adelt、Hans-Josef Altenbach

  DOI：10.1002/ejoc.200200572

  日期：2003.5

  practical route is described for the flexible preparation of a wide variety of inositol stereoisomers and their polyphosphates. The potential of this approach is demonstrated by the synthesis of myo-, L-chiro-, D-chiro-, epi-, scyllo-, allo-, and neo-inositol systems. Optically pure compounds in either enantiomeric form can be prepared from p-benzoquinone via enzymatic resolution of a derived conduritol B

  描述了灵活制备各种肌醇立体异构体及其多磷酸盐的实用途径。肌醇、L-手性、D-手性、epi-、scylo-、allo-和新肌醇系统的合成证明了这种方法的潜力。任一对映体形式的光学纯化合物可以通过衍生的 conduritol B 关键中间体的酶促拆分从对苯醌制备。带脉冲安培检测的高性能阴离子交换色谱允许以高灵敏度解析和检测肌醇立体异构体。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Flexible Stereo- and Regioselective Synthesis ofmyo-Inositol Phosphates(Part 1): Via Symmetrical Conduritol B Derivatives
  作者：Michael A. L. Podeschwa、Oliver Plettenburg、Hans-Josef Altenbach

  DOI：10.1002/ejoc.200400911

  日期：2005.7

  myo-inositol phosphates. Optically pure compounds can be prepared, in both forms, from p-benzoquinone by enzymatic resolution of a diacetoxyconduritol key intermediate. Monosubstituted inositol derivatives can be obtained by breaking the C2 symmetry of conduritol B derivatives. A wide variety of myo-inositol phosphates can be synthesized by combining the previously reported symmetrical approach with

  描述了用于制备肌醇磷酸酯的实用路线。通过酶促拆分二乙酰氧基硬糖醇关键中间体，可以从对苯醌制备两种形式的光学纯化合物。单取代的肌醇衍生物可以通过破坏 conduritol B 衍生物的 C2 对称性来获得。通过将先前报道的对称方法与这种新的非对称方法相结合，可以合成多种肌醇磷酸酯。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Regiospecific phosphohydrolases from Dictyostelium as tools for the chemoenzymatic synthesis of the enantiomers d-myo-inositol 1,2,4-trisphosphate and d-myo-inositol 2,3,6-trisphosphate: non-physiological, potential analogues of biologically active d-myo-inositol 1,3,4-trisphosphate
  作者：Stephan Adelt、Oliver Plettenburg、Guido Dallmann、Frank P Ritter、Stephen B Shears、Hans-Josef Altenbach、Günter Vogel

  DOI：10.1016/s0960-894x(01)00536-4

  日期：2001.10

  A new de novo synthesis of the enantiomeric pair D-myo-inositol 1,2,4-trisphosphate and D-myo-inositol 2,3,6-trisphosphate is described. Starting from enantiopure dibromocyclohexenediol, several C-2 Symmetrical building blocks were synthesized which gave access to D-myo-inositol 1,2,4,5-tetrakisphosphate and D-Myo-inositol 1,2,3,6-tetrakisphosphate. Exploiting the high regiospecificity of two partially purified phosphohydrolases from Dictyostelium, a 5-phosphatase and a phytase, the inositol tetrakisphosphates were converted enzymatically to the target compounds. Their potential to modulate the activity of Ins(3,4,5,6)P-4 I-kinase was investigated and compared with the effects Of D-myo-inositol 1,3,4-trisphosphate. (C) 2001 Elsevier Science Ltd. All rights reserved.