5,6-di-O-acetyl-1,4-bis-O-(di-O-benzylphospho)-2,3-bis-O-(3-oxo-1,5-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol | 281206-70-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-di-O-acetyl-1,4-bis-O-(di-O-benzylphospho)-2,3-bis-O-(3-oxo-1,5-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol
• 英文别名: [(1R,2R,3S,4R,5S,6S)-2-acetyloxy-3,6-bis[bis(phenylmethoxy)phosphoryloxy]-4,5-bis[(3-oxo-1,5-dihydro-2,4,3lambda5-benzodioxaphosphepin-3-yl)oxy]cyclohexyl] acetate；[(1R,2R,3S,4R,5S,6S)-2-acetyloxy-3,6-bis[bis(phenylmethoxy)phosphoryloxy]-4,5-bis[(3-oxo-1,5-dihydro-2,4,3λ5-benzodioxaphosphepin-3-yl)oxy]cyclohexyl] acetate
• CAS: 281206-70-0
• 化学式: C₅₄H₅₆O₂₀P₄
• 分子量: 1148.92
• InChiKey: VATOFNHUEPEELD-CFJXPGNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  78
• 可旋转键数：
  24
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  232
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  5,6-di-O-acetyl-1,4-bis-O-(di-O-benzylphospho)-2,3-bis-O-(3-oxo-1,5-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol 在 palladium on activated charcoal 氢气 作用下， 生成 Acetic acid (1R,2R,3S,4S,5R,6S)-2-acetoxy-3,4,5,6-tetrakis-phosphonooxy-cyclohexyl ester
  参考文献：
  名称：

  De novo synthesis of the enantiomers Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4—regiospecificity of their enzymatic dephosphorylation

  摘要：

  (T)he first total synthesis of Ins(1,2,3,4)P-4 and Ins(1,2,3,6)P-4 is presented. Starting from p-benzoquinone, we took advantage of the C-2-symmetry of conduritol-B intermediates. The target compounds were dephosphorylated by several enzymes, and the resulting InsP(3) isomers, were identified. Some of these enzymatic conversions were found to be preparatively applicable and to allow the synthesis of Ins(1,2,3)P-3, Ins(2,3,6)P-3 and Ins(1,2,4)P-3. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00063-x
• 作为产物：
  描述：

  (1S,2S,3S,4S)-anti-benzene dioxide 在 吡啶 、 四氮唑 、 ruthenium trichloride 、 sodium periodate 、 间氯过氧苯甲酸 作用下， 生成 5,6-di-O-acetyl-1,4-bis-O-(di-O-benzylphospho)-2,3-bis-O-(3-oxo-1,5-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol
  参考文献：
  名称：

  De novo synthesis of the enantiomers Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4—regiospecificity of their enzymatic dephosphorylation

  摘要：

  (T)he first total synthesis of Ins(1,2,3,4)P-4 and Ins(1,2,3,6)P-4 is presented. Starting from p-benzoquinone, we took advantage of the C-2-symmetry of conduritol-B intermediates. The target compounds were dephosphorylated by several enzymes, and the resulting InsP(3) isomers, were identified. Some of these enzymatic conversions were found to be preparatively applicable and to allow the synthesis of Ins(1,2,3)P-3, Ins(2,3,6)P-3 and Ins(1,2,4)P-3. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00063-x

文献信息

• 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)