D-6-deoxy-myo-inositol 1,4,5-trisphosphate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-6-deoxy-myo-inositol 1,4,5-trisphosphate
• 英文别名: [(1S,2R,3S,4R,5R)-2,3-dihydroxy-4,5-diphosphonooxycyclohexyl] dihydrogen phosphate
• 化学式: C₆H₁₅O₁₄P₃
• 分子量: 404.098
• InChiKey: GFBCCYAUTYOZMC-GNFDWLABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  241
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  D-2,3-O-cyclohexylidene-6-deoxy-myo-inositol-1,4,5-tris(dibenzyl)phosphate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 D-6-deoxy-myo-inositol 1,4,5-trisphosphate
  参考文献：
  名称：

  Stereoselective synthesis of inositol mono, bis and trisphosphate analogues from 6-deoxy- d -inositol precursors

  摘要：

  The synthesis of opticaly pure deoxy-myo-inositol mono, bis and trisphosphate analogues is described from 4-O-benzyl-2,3-di-O-cyclohexylidene-6-deoxy-myo-inositol and corresponding 1,5 epimer chiro-inositol. These precursors, which derive from galactose, are used to accede to a variety of cyclitol intermediates employing protection/deprotection sequence. The phosphorylation procedure was performed to produce free and original substituted phosphate derivatives aimed to be incorporated through the lipidic cell membrane for in vivo evaluation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00365-8

文献信息

• Microbial oxidation in synthesis: Preparation of 6-deoxy cyclitol analogues of myo-inositol 1,4,5-trisphosphate from benzene
  作者：Steven V. Ley、Margarita Parra、Alison J. Redgrave、Francine Sternfeld、Angel Vidal

  DOI：10.1016/s0040-4039(00)99439-5

  日期：1989.1

  The novel 6-deoxy, 6-deoxy-6-fluoro and 6-deoxy-6-methyl myo-inositol 1,4,5-trisphosphate derivatives (4), (5) and (6) were derived from benzene via microbial oxidation to cis-1,2-dihydroxycyclohexa-3,5-diene (2) and conversion through to the key epoxyacetonide (7).

  新型的6-脱氧，6-脱氧-6-氟和6-脱氧-6-甲基肌醇1,4,5-三磷酸酯衍生物（4），（5）和（6）是通过微生物氧化从苯衍生而来的生成顺式1,2-二羟基环己-3,5-二烯（2）并转化为关键的环氧丙酮化物（7）。
• Ley, Steven V.; Parra, Margarita; Redgrave, Alison J., Tetrahedron, 1990, vol. 46, # 13/14, p. 4994 - 5026
  作者：Ley, Steven V.、Parra, Margarita、Redgrave, Alison J.、Sternfeld, Francine

  DOI：——

  日期：——
• Synthesis, Acid−Base Behavior, and Binding Properties of 6-Modified <i>myo</i>-Inositol 1,4,5-Tris(phosphate)s
  作者：Stéphanie Ballereau、Philippe Guédat、Stéphane N. Poirier、Gaétan Guillemette、Bernard Spiess、Gilbert Schlewer

  DOI：10.1021/jm991084t

  日期：1999.11.1

  myo-Inositol 1,4,5-tris(phosphate) was modified at position 6. The analogues synthesized are reported in this publication are 6-deoxy-myo-inositol 1,4,5-tris(phosphate), 6-fluoro-6-deoxy-myo-inositol 1,4,5-tris(phosphate), epi-inositol 1,4,5-tris(phosphate), and 6-amino-6-deoxy-myo-inositol 1,4,5-tris(phosphate). These derivatives showed poor affinity for the Ins(1,4,5)P-3 receptors. The inframolecular acid-base behavior and the cooperative effects between the phosphate groups could help explain the loss of affinity of these 6-modified analogues.
• Stereoselective synthesis of inositol mono, bis and trisphosphate analogues from 6-deoxy- d -inositol precursors
  作者：Mauro Vieira de Almeida、Didier Dubreuil、Jeannine Cleophax、Catherine Verre-Sebrié、Muriel Pipelier、Guillaume Prestat、Georges Vass、Stéphane D Gero

  DOI：10.1016/s0040-4020(99)00365-8

  日期：1999.6

  The synthesis of opticaly pure deoxy-myo-inositol mono, bis and trisphosphate analogues is described from 4-O-benzyl-2,3-di-O-cyclohexylidene-6-deoxy-myo-inositol and corresponding 1,5 epimer chiro-inositol. These precursors, which derive from galactose, are used to accede to a variety of cyclitol intermediates employing protection/deprotection sequence. The phosphorylation procedure was performed to produce free and original substituted phosphate derivatives aimed to be incorporated through the lipidic cell membrane for in vivo evaluation. (C) 1999 Elsevier Science Ltd. All rights reserved.