allyl 2,6-di-trimethylacetyl-3,4-O-isopropylidene-α-D-glucopyranoside | 314252-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: allyl 2,6-di-trimethylacetyl-3,4-O-isopropylidene-α-D-glucopyranoside
• 英文别名: [(3aR,4R,6S,7R,7aS)-7-(2,2-dimethylpropanoyloxy)-2,2-dimethyl-6-prop-2-enoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl 2,2-dimethylpropanoate
• CAS: 314252-93-2
• 化学式: C₂₂H₃₆O₈
• 分子量: 428.523
• InChiKey: CSCWTPQIGJYFSZ-UUAJXVIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  allyl 2,6-di-trimethylacetyl-3,4-O-isopropylidene-α-D-glucopyranoside 在 sodium hydroxide 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 allyl 2,6-di-O-benzyl-3,4-O-isopropylidene-α-D-glucopyranoside
  参考文献：
  名称：

  C-Glycoside based mimics of d-myo-inositol 1,4,5-trisphosphate

  摘要：

  Epimeric C-glycoside based polyphosphates, alpha- and beta-D-glucopyranosylmethanol 3,4,1'-trisphosphates (8 and 9) were prepared from D-glucose. The key intermediate, allyl 2,6-di-O-benzyl-alpha-D-glucopyranoside, was prepared in five steps (67% yield) from allyl alpha-D-glucopyranoside without the need for chromatography. Compounds 8 and 9 were shown to be full agonists at the Ins(1,4,5)P-3 receptors of permeabilised hepatocytes, but with markedly different potencies. Such C-glycoside analogues are worthy of further development as Ins(1,4,5)P-3 receptor ligands. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00175-0
• 作为产物：
  描述：

  烯丙基-alpha-D-吡喃葡萄糖苷 在 吡啶 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 生成 allyl 2,6-di-trimethylacetyl-3,4-O-isopropylidene-α-D-glucopyranoside
  参考文献：
  名称：

  针对潜在的第二钙通道IP3受体的新型吡喃糖苷衍生物的设计，合成和杀虫活性

  摘要：

  为了搜索与新的作用方式，一系列吡喃糖苷衍生物模仿D-的有效且环保的杀虫剂肌醇肌醇1,4,5-三磷酸（IP 3）根据所述生物电子等排的方法设计和合成。生物学测定表明，大多数新化合物对东方粘虫（Mythimna separata）和小菜蛾（Plutella xylostella）表现出中等至良好的杀虫活性。尤其是，化合物5g在50 mg / L下对东方粘虫表现出80％的杀幼虫活性。同时5a分别对50和25 mg / L的小菜蛾有100％和70％的杀幼虫活性。为了进一步探讨其作用方式，采用钙成像技术研究了5a，5g和5i对从斜纹夜蛾分离的中枢神经元细胞内钙离子浓度（[Ca 2+ ] i）的影响。结果表明，所测试的化合物从内质网释放了储存的钙离子。

  DOI：

  10.1002/cjoc.201600460

文献信息

• Design, Synthesis, and Insecticidal Activities of Novel Pyranoside Derivatives Targeting at Potential Second Calcium Channel IP₃Receptor
  作者：Changchun Wu、Yuxin Li、Ming Liu、Jingbo Liu、Xuewen Hua、Dongkai Zhang、Lixia Xiong、Na Yang、Baolei Wang、Zhengming Li

  DOI：10.1002/cjoc.201600460

  日期：2016.11

  In order to search for potent and environmental friendly insecticides with new modes of action, a series of pyranoside derivatives mimicking D‐myo‐inositol 1,4,5‐trisphosphate (IP3) were designed and synthesized according to the bioisosteric approach. The biological assay indicated that most of the new compounds showed moderate to good insecticidal activities against oriental armyworm (Mythimna separata)

  为了搜索与新的作用方式，一系列吡喃糖苷衍生物模仿D-的有效且环保的杀虫剂肌醇肌醇1,4,5-三磷酸（IP 3）根据所述生物电子等排的方法设计和合成。生物学测定表明，大多数新化合物对东方粘虫（Mythimna separata）和小菜蛾（Plutella xylostella）表现出中等至良好的杀虫活性。尤其是，化合物5g在50 mg / L下对东方粘虫表现出80％的杀幼虫活性。同时5a分别对50和25 mg / L的小菜蛾有100％和70％的杀幼虫活性。为了进一步探讨其作用方式，采用钙成像技术研究了5a，5g和5i对从斜纹夜蛾分离的中枢神经元细胞内钙离子浓度（[Ca 2+ ] i）的影响。结果表明，所测试的化合物从内质网释放了储存的钙离子。
• C-Glycoside based mimics of d-myo-inositol 1,4,5-trisphosphate
  作者：Heidi J. Rosenberg、Andrew M. Riley、Vanessa Correa、Colin W. Taylor、Barry V.L. Potter

  DOI：10.1016/s0008-6215(00)00175-0

  日期：2000.10

  Epimeric C-glycoside based polyphosphates, alpha- and beta-D-glucopyranosylmethanol 3,4,1'-trisphosphates (8 and 9) were prepared from D-glucose. The key intermediate, allyl 2,6-di-O-benzyl-alpha-D-glucopyranoside, was prepared in five steps (67% yield) from allyl alpha-D-glucopyranoside without the need for chromatography. Compounds 8 and 9 were shown to be full agonists at the Ins(1,4,5)P-3 receptors of permeabilised hepatocytes, but with markedly different potencies. Such C-glycoside analogues are worthy of further development as Ins(1,4,5)P-3 receptor ligands. (C) 2000 Elsevier Science Ltd. All rights reserved.