Methanesulfonic acid (3aS,4R,4aS,7aR,8S,8aS)-8-benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl ester | 192068-52-3

• 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: Methanesulfonic acid (3aS,4R,4aS,7aR,8S,8aS)-8-benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl ester
• CAS: 192068-52-3
• 化学式: C₂₀H₂₈O₈S
• 分子量: 428.504
• InChiKey: GMDJKIOXGFKSOD-MCEUPANISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (3aS,4R,4aS,7aR,8S,8aS)-8-benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl ester 在 乙酰氯 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 锂硼氢 、 草酰氯 、 sodium methylate 、 sodium hydride 、 二甲基亚砜 、 二异丙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 93.25h， 生成 (1S,2S,3R,4S,5S,6R)-6-[(4-methoxyphenyl)methoxy]-3-phenylmethoxy-5-(phenylmethoxymethoxy)cyclohexane-1,2,4-triol
  参考文献：
  名称：

  Tools for Cell Signaling: Synthesis of the 3-Phosphatase-Resistant 1,3,4,5-InsP4 Mimic, 1D-myo-Inositol 1,4,5-Trisphosphate 3-Phosphorothioate

  摘要：

  The synthesis of 1D-myo-inositol 1,4,5-trisphosphate 3-phosphorothioate, a 3-phosphatase-resistant analogue of 1,3,4,5-InsP(4) is reported, and this compound is shown to elicit Ca-45(2+) release with an EC(50) which is comparable to that of the natural metabolite, thus supporting the idea that 1,3,4,5-InsP(4) can interact with the 1,4,5-InsP(3) receptors.

  DOI：

  10.1021/jo00088a003
• 作为产物：
  描述：

  1L-3,4:5,6-Di-O-isopropyliden-2-O-methyl-chiro-inosit 在 TEA 、 camphor-10-sulfonic acid 、 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 Methanesulfonic acid (3aS,4R,4aS,7aR,8S,8aS)-8-benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl ester
  参考文献：
  名称：

  Tools for Cell Signaling: Synthesis of the 3-Phosphatase-Resistant 1,3,4,5-InsP4 Mimic, 1D-myo-Inositol 1,4,5-Trisphosphate 3-Phosphorothioate

  摘要：

  The synthesis of 1D-myo-inositol 1,4,5-trisphosphate 3-phosphorothioate, a 3-phosphatase-resistant analogue of 1,3,4,5-InsP(4) is reported, and this compound is shown to elicit Ca-45(2+) release with an EC(50) which is comparable to that of the natural metabolite, thus supporting the idea that 1,3,4,5-InsP(4) can interact with the 1,4,5-InsP(3) receptors.

  DOI：

  10.1021/jo00088a003

文献信息

• 1D-myo-inositol 1,4,5-trisphosphate and 1D-myo-inositol 1,3,4,5-tetrakisphosphate analogues modified at C-3; synthesis of 1D-3-C-(trifluoromethyl)-myo-inositol 1,4,5-trisphosphate and 1L-chiro-insitol 1,2,3,5-tetrakisphosphate from L-quebrachitol
  作者：Alan P. Kozikowski、Vassil I. Ognyanov、Abdul H. Fauq、Robert A. Wilcox、Stefan R. Nahorski

  DOI：10.1039/c39940000599

  日期：——

  The novel 3-modified 1D-myo-inositol 1,4,5-trisphosphate [Ins(1,4,5)P3] analogues 1D-3-C-(trifluoromethyl)-myo-inositol 1,4,5-trisphosphate and 1L-chiro-inositol 1,2,3,5-tetrakisphosphate are synthesized from L-quebrachitol, and the preliminary results on their Ca2+ releasing activity suggest that the Ins(1,4,5)P3 receptor can accommodate some steric bulk in the axial region of the 3-position of Ins(1,4,5)P3 when the equatorial 3-hydroxy group is retained.

  新型 3-修饰 1D-肌醇 1,4,5-三磷酸[Ins(1,4,5)P3]类似物 1D-3-C-(trifluoromethyl)-myo-inositol 1,4,5-trisphosphate 和 1L-chiro-inositol 1,2,3,5-tetrakisphosphate 由 L- 曲波胆糖醇合成、关于它们释放 Ca2+ 活性的初步研究结果表明，当保留 Ins(1,4,5)P3 3-位的赤道 3-羟基时，Ins(1,4,5)P3 受体可以在 3-位的轴向区域容纳一些立体体积。