(1R,2S,3R,4R,5S)-2,3,4,5-tetrakis(benzyloxy)cyclohexanol | 143396-09-2

• 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: (1R,2S,3R,4R,5S)-2,3,4,5-tetrakis(benzyloxy)cyclohexanol
• 英文别名: D-2-deoxy-3,4,5,6-tetra-O-benzyl-myo-inositol；(1R,2S,3R,4R,5S)-2,3,4,5-tetrakis(phenylmethoxy)cyclohexan-1-ol
• CAS: 143396-09-2
• 化学式: C₃₄H₃₆O₅
• 分子量: 524.657
• InChiKey: CZRDPDBEPJTKER-BWNLSPMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4R,5S)-2,3,4,5-tetrakis(benzyloxy)cyclohexanol 在 sodium azide 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  EP2409966

  摘要：

  公开号：
• 作为产物：
  描述：

  3,4,5,6-tetra-O-benzyl-1-O-p-methoxybenzyl-D-myo-inositol 在 咪唑 、 偶氮二异丁腈 、 水 、 碘 、 三正丁基氢锡 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 43.47h， 生成 (1R,2S,3R,4R,5S)-2,3,4,5-tetrakis(benzyloxy)cyclohexanol
  参考文献：
  名称：

  2-Deoxy Derivative Is a Partial Agonist of the Intracellular Messenger Inositol 3,4,5,6-Tetrakisphosphate in the Epithelial Cell Line T₈₄

  摘要：

  We have synthesized the first deoxy analogues of myo-inositol 3,4,5,6-tetrakisphosphate (1) [Ins(3,4,5,6)P-4], rac-2-deoxy-myo-inositol 3,4,5,6-tetrakisphosphate (rac-2), 2-deoxy-myo-inositol 1,4,5,6-tetrakisphosphate (ent-2), and rac-1-deoxy-myo-inositol 3,4,5,6-tetrakisphosphate (rac-3). In order to evaluate the binding properties of the three derivatives to the yet unidentified intracellular binding sites for Ins(3,4,5,6)P4, the analogues were converted to membrane-permeant derivatives. Starting with common inositol precursors, various forms of Barton-McCombie deoxygenation and classical protection/deprotection procedures yielded the desired precursors rac-1-O-butyryl-2-deoxy-myo-inositol (rac-12), ent-3-O-butyryl-2-deoxy-myo-inositol (ent-12), and rac-2-O-butyryl-1-deoxy-myo-inositol (rac-19), respectively. Phosphorylation and subsequent deprotection yielded rac-2, ent-2, and rac-3. Alternatively, phosphorylation followed by alkylation with acetoxymethyl bromide gave the membrane-permeant derivatives 1-O-butyryl-2-deoxy-myo-inositol 3,4,5,6-tetrakisphosphate octakis(acetoxymethyl) ester (rac-5), 3-O-butyryl-2-deoxy-myo-inositol 1,4,5,6-tetrakisphosphate octakis(acetoxymethyl) ester (ent-5), and 2-O-butyryl-1-deoxy-myo-inositol 3,4,5,6-tetrakisphosphate octakis(acetoxymethyl) ester (rac-6), respectively. We examined the potency of the membrane-permeant deoxy derivatives in inhibition of calcium-mediated chloride secretion (CaMCS) in intact T-84 cells. Compared to the 1,2-di-O-butyryl-myo-inositol 3,4,5,6-tetrakisphosphate octakis(acetoxymethyl) ester (4), the membrane-permeant derivative of Ins(3,4,5,6)P-4 (1), the 2-deoxy derivative (rac-5) exhibited a slightly weaker inhibitory effect, while the enantiomerically pure 2-deoxy-Ins(1,4,5,6)P-4 (ent-5) and the l-deoxy derivative (rac-6) were inactive. As expected, the effect was stereoselective. Thus, the l-hydroxyl group is apparently essential for binding and the inhibitory effect of Ins(3,4,5,6)P4 on chloride secretion, whereas the 2-hydroxyl group plays a less important role.

  DOI：

  10.1021/jm970781n

文献信息

• The synthesis of homochiral inositol phosphates from myo-inositol
  作者：K.Michał Pietrusiewicz、Grzegorz M. Salamończyk、Karol S. Bruzik、Wanda Wieczorek

  DOI：10.1016/s0040-4020(01)88305-8

  日期：1992.1

  conversion of myo-inositol into homochiral inositol phosphates is presented, and is illustrated with total synthesis of myo-inositol 1-phosphate, 2-deoxy-myo-inositol 1-phosphate, myo-inositol 3-phosphate, myo-inositol 4-phosphate, myo-inositol 1,4-bisphosphate, myo-inositol 1,4,5-trisphosphate, and myo-inositol 3,4,5,6-tetrakisphosphate. The syntheses start with selfresolving myo-inositol camphanylidene

  高效转换的一个新的合成方法肌醇肌醇成纯手性肌醇磷酸被呈现，并且与全合成所示肌醇-1-磷酸，2-脱氧肌醇-1-磷酸，肌醇肌醇-3-磷酸，肌肌醇-4-磷酸，肌醇肌醇1,4-二磷酸，肌醇肌醇1,4,5-三磷酸和肌醇肌醇3,4,5,6-四磷酸盐。该合成开始selfresolving肌肌醇camphanylidene顺-monoacetals 2A和2A'分别从母体环糖醇和D-和L-樟脑二甲基缩醛一步获得，并通过沉淀驱动的平衡方便地收获。合成的关键步骤是2a和2a'的选择性单磷酸化，选择性双甲硅烷基化和选择性三酰基化，以及使用二氯磷酸二苄酯和2-二甲氨基-5,6-苯并-1,3,2-二氧杂磷杂环戊烷来实现单磷酸化和多磷酸化。为了支持立体化学分配，还提出了一种中间体完全保护的肌醇衍生物之一的X射线结构。
• Synthesis of 2- and 6-deoxyinositol 1-phosphate and the role of the adjacent hydroxy groups in the mechanism of inositol monophosphatase
  作者：Raymond Baker、Janusz J. Kulagowski、David C. Billington、Paul D. Leeson、Ian C. Lennon、Nigel Liverton

  DOI：10.1039/c39890001383

  日期：——

  The 2- and 6-hydroxy groups of myo-inositol 1-phosphate have been shown to be independently associated with the mechanisms of hydrolysis and binding in the dephosphorylation of the substrate by inositol monophosphatase.

  的2-和6-羟基肌醇-1-磷酸已显示与水解并且在由肌醇单磷酸酶的底物的去磷酸化的结合的机制来独立地相关联。
• AMINOCYCLITOL COMPOUNDS, PROCESS FOR OBTAINING THEM AND USES
  申请人：Llebaria Soldevilla Amadeo

  公开号：US20120093875A1

  公开（公告）日：2012-04-19

  Aminocyclitol compounds and uses thereof as pharmaceutical compositions for the treatment of diseases associated with alterations in iNKT cells, more specifically autoimmune diseases, cancer, infections caused by pathogenic microorganisms or inflammatory diseases. Furthermore, the invention relates to the process for obtaining said compounds.

  氨基环糖醇化合物及其用途作为制药组合物治疗与iNKT细胞变化相关的疾病，更具体地包括自身免疫性疾病、癌症、由致病微生物引起的感染或炎症性疾病。此外，本发明还涉及获得该化合物的过程。
• Elaboration of a General Strategy for Inhibition of myo-Inositol 1-Phosphate Synthase:  Active Site Interactions of Analogues Possessing Oxidized Reaction Centers
  作者：Marie E. Migaud、J. W. Frost

  DOI：10.1021/ja952570i

  日期：1996.1.1

  In addition to being an intermediate along the reaction coordinate catalyzed by myo-inositol 1-phosphate (MIP) synthase, myo-2-inosose 1-phosphate is a 3.6 μM competititve inhibitor of the enzyme at pH 7.2. To probe the importance of the oxidized reaction center in myo-2-inosose 1-phosphate to active site interactions and gauge the relative contribution of the keto form to these interactions, three

  除了作为由肌醇 1-磷酸 (MIP) 合酶催化的反应坐标的中间体之外，肌醇 1-磷酸在 pH 7.2 时还是该酶的 3.6 μM 竞争性抑制剂。为了探究 myo-2-inosose 1-phosphate 中氧化反应中心对活性位点相互作用的重要性并衡量酮形式对这些相互作用的相对贡献，已经检查了三种类似物的 MIP 合酶抑制作用。2-Deoxy-myo-inositol 1-phosphate 用于衡量去除 myo-2-inosose 1-磷酸的氧化反应中心的影响。1-Deoxy-1-(膦酰基甲基)-myo-2-inosose，用亚甲基取代 myo-2-inosose 1-磷酸的磷酸单酯氧，仅以其酮形式存在于中性水溶液中。磷酸二羟丙酮为抑制 MIP 合酶的最低结构要求提供了见解。2-Deoxy-myo-inositol 1-phosphate 是一种 170 μM 竞争性抑制剂，pH 7.2，这是一种
• AMINOCYCLITOL COMPOUNDS, PROCEDURE FOR THE OBTAINMENT AND USES
  申请人：Consejo Superior de Investigaciones Cientificas (CSIC)

  公开号：EP2409966A1

  公开（公告）日：2012-01-25

  Aminocyclitol compounds, process for obtaining them and uses Aminocyclitol compounds and uses thereof as pharmaceutical compositions for the treatment of diseases associated with alterations in iNKT cells, more specifically autoimmune diseases, cancer, infections caused by pathogenic microorganisms or inflammatory diseases. Furthermore, the invention relates to the process for obtaining said compounds,

  氨基环醇化合物、其获得方法和用途 本发明涉及氨环醇类化合物及其作为药物组合物的用途，用于治疗与 iNKT 细胞改变有关的疾病，特别是自身免疫性疾病、癌症、病原微生物引起的感染或炎症性疾病。此外，本发明还涉及获得上述化合物的工艺、