2,4,6-tris-O-para-methoxybenzyl-myo-inositol | 155666-58-3

• 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: 2,4,6-tris-O-para-methoxybenzyl-myo-inositol
• 英文别名: 2,4,6-tris-O-(p-methoxybenzyl)-myo-inositol；2,4,6-tri-O-(4-methoxybenzyl)-myo-inositol；2,4,6-tri-O-p-methoxybenzyl-D-myo-inositol
• CAS: 155666-58-3
• 化学式: C₃₀H₃₆O₉
• 分子量: 540.61
• InChiKey: AWTRHKHVNWAMNH-NJCCCCKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  116.07
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2,4,6-tris-O-para-methoxybenzyl-myo-inositol 在 吡啶 、 四氮唑 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2,4,6-tris-O-(p-methoxybenzyl)-1,3,5-tris--myo-inositol
  参考文献：
  名称：

  Synthesis of Selective Non-Ca2+ Mobilizing Inhibitors of D-myo-Inositol 1,4,5-Trisphosphate 5-Phosphatase

  摘要：

  Syntheses of novel phosphorothioate-based non-Ca2+-releasing inhibitors of myo-inositol 1,4,5-trisphosphate 5-phosphatase are described. 1L-myo-Inositol 1,4,5-trisphosphorothioate, myoinositol 1,3,5-trisphosphorothioate, and 1L-chiro-inositol 1,4,6-trisphosphorothioate have been synthesized from 1L-2,3,6-tri-O-benzyl-1-O-(cis-prop-1-enyl)-myo-inositol, 2,4,6-tris-O-(p-methoxybenzyl)-myo-inositol orthoformate and 1L-2,3,5-tri-O-benzyl-chiro-inositol, respectively. 1L-2,3,5-Tri-O-benzyl-chiro-inositol was also used to prepare 1L-chiro-inositol 1,4,6-trisphosphate. The phosphorothioates did not mobilize intracellular Ca2+ but were highly potent inhibitors of Ins(1,4,5)P(3)5-phosphatase, and myo-inositol 1,3,5-trisphosphorothioate and 1L-chiro-inositol 1,4,6-trisphosphorothioate were selective for this enzyme.

  DOI：

  10.1021/jm00033a007
• 作为产物：
  描述：

  4-甲氧基氯苄 在 盐酸 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 2,4,6-tris-O-para-methoxybenzyl-myo-inositol
  参考文献：
  名称：

  [EN] CALCIUM OXALATE CRYSTALLIZATION INHIBITORS FOR RENAL DISORDERS
  [FR] INHIBITEURS DE CRISTALLISATION D'OXALATE DE CALCIUM POUR TROUBLES RÉNAUX

  摘要：

  本发明涉及含有两个或更多个环己醇五酯基团的肌醇衍生物，这些基团通过共同的中心连接物连接在一起，并且它们在治疗或预防与病理结晶有关的疾病中的用途。该发明还涉及合成本发明化合物中有用的中间体。

  公开号：

  WO2020058321A1

文献信息

• Unified Total Syntheses of the Inositol Polyphosphates:  <scp>d</scp>-I-3,5,6P₃, <scp>d</scp>-I-3,4,5P₃, <scp>d</scp>-I-3,4,6P₃, and <scp>d</scp>-I-3,4,5,6P₄ via Catalytic Enantioselective and Site-Selective Phosphorylation
  作者：Adam J. Morgan、Shio Komiya、Yingju Xu、Scott J. Miller

  DOI：10.1021/jo0610816

  日期：2006.9.1

  Synthetic routes to various inositol polyphosphates have been discovered utilizing catalytic enantioselective and site-selective phosphorylation reactions. The syntheses described herein exploit a common intermediate to gain efficient access to eight unique inositol polyphosphates.

  已经利用催化对映选择性和位点选择性磷酸化反应发现了合成各种肌醇多磷酸盐的途径。本文所述的合成方法利用一种常见的中间体来有效地获得八种独特的肌醇多磷酸酯。
• Streamlined Synthesis of Phosphatidylinositol (PI), PI3P, PI3,5P₂, and Deoxygenated Analogues as Potential Biological Probes
  作者：Yingju Xu、Bianca R. Sculimbrene、Scott J. Miller

  DOI：10.1021/jo060702s

  日期：2006.6.1

  Highly direct total syntheses of phosphatidylinositol (PI), phosphatidylinositol-3-phosphate (PI3P), phosphatidylinositol-3,5-bisphosphate (PI3,5P2), and a range of deoxygenated versions are reported. Each synthesis is carried out to deliver the target in optically pure form. The key step for each synthesis is a catalytic asymmetric phosphorylation reaction that affects desymmetrization of an appropriate

  据报道，磷脂酰肌醇（PI），磷脂酰肌醇-3-磷酸酯（PI3P），磷脂酰肌醇-3,5-双磷酸酯（PI3,5P 2）和一系列脱氧形式的高度直接的全合成。进行每个合成以递送光学纯形式的靶标。对于每个合成中的关键步骤是催化不对称磷酸化反应，影响适当的desymmetrization肌醇-肌醇的前体。然后采用通用前体的面向多样性的策略对每种目标化合物进行精细加工。除三种天然产物外，还报道了几种其他简化的脱氧PI类似物的总合成方法。这些合成为这些膜相关信号分子的极性头基/生物靶标相互作用的高精度生物学研究奠定了基础。
• PHARMACEUTICAL COMPOUNDS FOR USE IN THE THERAPY OF CLOSTRIDIUM DIFFICILE INFECTION
  申请人：ETH ZURICH

  公开号：US20140235590A1

  公开（公告）日：2014-08-21

  The invention relates to a compound described by a general formula (1), wherein each X independently can be OPO 3 2− , OPSO 2 2− or OSO 3 − ; R 1 comprises a solubility function such as a polyethylene glycol moiety and each X independently can be OPO 3 2− , OPSO 2 2− , − or OSO 3 − ; and Z is an alkyl chain comprising 1 to 3 carbon and/or hetero atoms. The invention further relates to polysulfate derivatives or mixed polyphosphate/sulphate derivatives of six-membered cyclic polyols for use in the therapy of infection by Clostridium difficile.

  本发明涉及一种由一般式（1）描述的化合物，其中每个X可以独立地是OPO32−、OPSO22−或OSO3−；R1包括诸如聚乙二醇基团之类的溶解度功能，每个X可以独立地是OPO32−、OPSO22−或OSO3−；Z是由1到3个碳和/或杂原子组成的烷基链。本发明还涉及六元环多醇的聚硫酸盐衍生物或混合聚磷酸盐/硫酸盐衍生物，用于治疗ClOStridium difficile感染。
• [EN] PHARMACEUTICAL COMPOUNDS FOR USE IN THE THERAPY OF CLOSTRIDIUM DIFFICILE INFECTION<br/>[FR] COMPOSÉS PHARMACEUTIQUES POUR UTILISATION DANS LA THÉRAPIE D'UNE INFECTION PAR CLOSTRIDIUM DIFFICILE
  申请人：ETH ZUERICH

  公开号：WO2013045107A1

  公开（公告）日：2013-04-04

  The invention relates to a compound described by a general formula (1), wherein each X independently can be OPO32-, OPSO22- or OSO3-; R1 comprises a solubility function such as a polyethylene glycol moiety and each X independently can be OPO32-, OPSO22-, - or OSO3-; and Z is an alkyl chain comprising 1 to 3 carbon and/or hetero atoms. The invention further relates to polysulfate derivatives or mixed polyphosphate/sulphate derivatives of six-membered cyclic polyols for use in the therapy of infection by Clostridium difficile.

  本发明涉及一种由普遍式（1）描述的化合物，其中每个X独立地可以是OPO32-，OPSO22-或OSO3-；R1包括溶解性功能，例如聚乙二醇基团，每个X独立地可以是OPO32-，OPSO22-或OSO3-；而Z是一个含有1到3个碳和/或杂原子的烷基链。本发明还涉及六元环多元硫酸盐衍生物或混合多聚磷酸盐/硫酸盐衍生物，用于治疗难辨梭菌感染。
• Asymmetric Syntheses of Phosphatidylinositol-3-Phosphates with Saturated and Unsaturated Side Chains through Catalytic Asymmetric Phosphorylation
  作者：Bianca R. Sculimbrene、Yingju Xu、Scott J. Miller

  DOI：10.1021/ja0466098

  日期：2004.10.1

  Highly direct asymmetric syntheses of phosphatidylinositol-3-phosphate (PI3P) in each enantiomerically pure form have been achieved. The key step involves catalytic asymmetric phosphorylation of meso-myo-inositol derivatives through desymmetrization. Protecting group schemes have been employed that allow for synthesis of PI3P with either saturated or arachidonate side chains, in analogy to the naturally occurring systems. Syntheses in each enantiomeric series are reported that rely on the choice of enantioselective peptide-based catalyst to define the enantiomeric series in which the syntheses are carried out.