1D-3-deoxy-1,2:4,5-di-O-isopropylidene-myo-inositol | 132662-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1D-3-deoxy-1,2:4,5-di-O-isopropylidene-myo-inositol
• 英文别名: 1,2:4,5-di-O-isopropylidene-L-vibo-quercitol
• CAS: 132662-64-7
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: GZAUSEVVFGFLES-GRDBIXFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (-)-VIBO-栎醇 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 1D-3-deoxy-1,2:4,5-di-O-isopropylidene-myo-inositol 、 1D-3-deoxy-1,2:5,6-di-O-isopropylidene-myo-inositol
  参考文献：
  名称：

  Design and synthesis of glycosidase inhibitor 5-amino-1,2,3,4-cyclohexanetetrol derivatives from (−)-vibo-quercitol

  摘要：

  In continuation of development of bioactive inositol derivatives, a 1-O-methyl derivative of 5-amino-5-deoxy-L-talo-quercitol was designed and synthesized as an analogue of the strong alpha-fucosidase inhibitor, 5a-carba-alpha-L-fucopyranosylamine, the methyl branch being replaced with methoxyl, and demonstrated to be a moderate alpha-fucosidase inhibitor. The present approach provides a possible route to apply alkyl ethers of aminodeoxymositols as hexopyranose mimics of biological interest. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.003

文献信息

• Synthesis of D-3-deoxy-myo-inositol 1,4,5-trisphosphate and its effect on Ca2+ release in NIH 3T3 cells
  作者：Markus J. Seewald、Ibrahim A. Aksoy、Garth Powis、Abdul H. Fauq、Alan P. Kozikowski

  DOI：10.1039/c39900001638

  日期：——

  The synthesis of D-3-deoxy-myo-inositol 1,4,5-trisphosphate is reported together with its effect on Ca2+ release in permeabilized NIH 3T3 cells.

  d-3 -脱氧的合成肌肉肌醇1,4,5-三磷酸与其对Ca效果一起报告2+在透化的NIH 3T3细胞的释放。
• Synthesis of 1D-3-deoxy-, 1D-2,3-dideoxy-, and 1D-2,3,6-trideoxy-myo-inositol 1,4,5-trisphosphate from quebrachitol, their binding affinities, and calcium release activity
  作者：A. P. Kozikowski、V. I. Ognyanov、A. H. Fauq、S. R. Nahorski、R. A. Wilcox

  DOI：10.1021/ja00064a002

  日期：1993.6

  Syntheses of three optically pure, deoxygenated myo-inositol 1,4,5-trisphosphate analogues from quebrachitol are reported together with their binding affinities and 45 Ca 2+ release activity. The ligand-binding affinities of the analogues were determined using membrane preparations from bovine adrenal cortex. The 45 Ca 2+ release activities were compared to that of Ins(1,4,5)P 3 , using the calcium

  三种光学纯的、脱氧的肌醇 1,4,5-三磷酸酯类似物的合成与它们的结合亲和力和 45 Ca 2+ 释放活性一起报告。使用来自牛肾上腺皮质的膜制剂测定类似物的配体结合亲和力。45 Ca 2+ 释放活性与Ins(1,4,5)P 3 的释放活性进行了比较，使用皂苷透化的SH-SY5Y人神经母细胞瘤细胞的钙动员受体。1D-3-deoxy-Ins(1,4,5)P 3 (16) 和 1D-2,3-dideoxy-Ins(1,4,5)P 3 (11) 表现出非常有效的配体和激动剂特性，而1D-2,3,6-trideoxy-Ins(1,4,5)P 3 (19) 的效力要低得多。这些数据为 Ins(1,4,5)P 3 的 HO-6 在其结合亲和力和 Ca 2+ 动员活性中发挥的关键作用提供了确凿的证据
• Synthesis and evaluation of glucocerebrosidase inhibitory activity of anhydro deoxyinositols from (+)-epi-and(−)-vibo-quercitols
  作者：Seiichiro Ogawa、Satoko Uetsuki、Yoji Tezuka、Takayuki Morikawa、Atsushi Takahashi、Kiyoshi Sato

  DOI：10.1016/s0960-894x(99)00223-1

  日期：1999.6

  Twelve 1,2- and 2,3-anhydro-1,2,3,4,5-cyclohexanepentols were synthesized from (+)-epi- and (-)-vibo-quercitols, readily available by bioconversion of myo-inositol, and assayed for inhibitory activity against glucocerebrosidase (mouse liver). Among them 1L-1,2-anhydro-1,2,4/3,5-cyclohexanepentol, the 3-deoxy derivative of the irreversible inhibitor conduritol B epoxide (CBE), has been demonstrated to be a highly potent and specific inhibitor, almost comparable to the parent compound. (C) 1999 Elsevier Science Ltd. All rights reserved.