(1S,2S,3S,4S)-1,4-bis(di-O-benzylphospho)conduritol-B | 222420-77-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3S,4S)-1,4-bis(di-O-benzylphospho)conduritol-B
• 英文别名: (1S,2R,3R,4S)-1,4-bis-O-(di-O-benzylphospho)conduritol B；dibenzyl [(1S,4S,5S,6S)-4-bis(phenylmethoxy)phosphoryloxy-5,6-dihydroxycyclohex-2-en-1-yl] phosphate
• CAS: 222420-77-1
• 化学式: C₃₄H₃₆O₁₀P₂
• 分子量: 666.601
• InChiKey: ABRUNQGQQHIPSG-PSWJWLENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,4S)-1,4-bis(di-O-benzylphospho)conduritol-B 在 palladium on activated charcoal ruthenium trichloride 、 sodium periodate 、 氢气 作用下， 以 水 、 乙腈 、 乙醇 为溶剂， 反应 0.17h， 以60 mg的产率得到myo-Inositol 1,4-diphosphate
  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：

  (1RS,2SR,3RS,4RS)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene 在 氢氧化钾 、 pig pancreas lipase 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,2S,3S,4S)-1,4-bis(di-O-benzylphospho)conduritol-B
  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

• Enzyme-Assisted Total Synthesis of the Optical Antipodes <scp>d</scp>-<i>myo</i>-Inositol 3,4,5-Trisphosphate and <scp>d</scp>-<i>myo</i>-Inositol 1,5,6-Trisphosphate:  Aspects of Their Structure−Activity Relationship to Biologically Active Inositol Phosphates
  作者：Stephan Adelt、Oliver Plettenburg、Rolf Stricker、Georg Reiser、Hans-Josef Altenbach、Günter Vogel

  DOI：10.1021/jm981113k

  日期：1999.4.1

  Unambiguous total syntheses of bath optical antipodes of the enantiomeric pair D-myo-inositol 3,4,5-trisphosphate (Ins(3,4,5)P-3) and D-myo-inositol 1,5,6-trisphosphate (Ins(1,5,6)P-3) are described. The ring system characteristic of myo-inositol was constructed de novo from p-benzoquinone. X-ray data for the enzymatically resolved (1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene enabled the unequivocal assignment of the absolute configuration. Subsequent transformations under stereocontrolled conditions led to enantiopure C-2-symmetrical 1,4-(di-O-benzyldiphospho)conduritol B derivatives. Their synthetic potential was exploited to prepare Ins(3,4,5,6)P-4 and Ins(1,4,5,6)P-4 in three steps. With a recently identified and partially purified InsP(5)/InsP(4) phosphohydrolase from Dictyostelium discoideum, these enantiomers could be converted to the target compounds, Ins(3,4,5)P-3 and Ins(1,5,6)P-3, on a preparative scale. An HPLC system employed for both purification of the inositol phosphates and analytical runs ensured that the products were isomerically homogeneous. The sensitivity of detection achieved by a complexometric postcolumn derivatization method indicates that the complexation properties of Ins(3,4,5)P-3/Ins(1,5,6)P-3 resemble those of Ins(1,2,3)P-3, a compound with antioxidantpotential. The set of inositol phosphates synthesized was used to clarify structural motifs important for molecular recognition by p42(IP4) , high-affinity Ins(1,3,4,5)P-4/PtdIns(3,4,5)P-3-specific binding protein from pig cerebellum.