3-O-methyl-4,5-epoxy-D-chiro-inositol | 18391-52-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 3-O-methyl-4,5-epoxy-D-chiro-inositol
• 英文别名: 2,3-Anhydro-1-O-methyl-alloinosit；(1S,2S,3R,4S,5R,6S)-5-methoxy-7-oxabicyclo[4.1.0]heptane-2,3,4-triol
• CAS: 18391-52-1
• 化学式: C₇H₁₂O₅
• 分子量: 176.169
• InChiKey: ZZFXHPYMGJJZKZ-URFJBAFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  82.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1H-1,2,4-三唑 、 3-O-methyl-4,5-epoxy-D-chiro-inositol 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以74%的产率得到(1'S,2'S,3'S,4'S,5'R,6'R)-3'-O-methyl-5'-deoxy-5'-(1,2,4-triazole-1-yl)-D-chiro-inositol
  参考文献：
  名称：

  Synthesis of azole nucleoside analogues of d-pinitol as potential antitumor agents

  摘要：

  A convenient strategy is reported for the synthesis of azole nucleoside analogues of D-pinitol (=3-O-methyl-D-chiro-inositol). The key intermediate 3-O-methyl-4,5-epoxy-D-chiro-inositol was obtained in excellent yield via an epoxidation from monomethanesulfonate Of D-pinitol. The process of opening of the epoxy ring by azole-bases appeared strongly regioselective in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene. All newly synthesized carbocyclic azole nucleosides were assayed against lung and bladder cancer in vitro. Only the triazole and benzotriazole nucleoside analogues inhibited the growth of human lung cancer cell lines (PG) with EC(50) of 11.3 and 22.6 mu M, respectively, and showed much less inhibitory activity against human bladder cell lines (T(24)). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.01.004
• 作为产物：
  描述：

  D-松醇 在 magnesium sulfate 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 吡啶 、 甲醇 、 丙酮 为溶剂， 反应 58.0h， 生成 3-O-methyl-4,5-epoxy-D-chiro-inositol
  参考文献：
  名称：

  Synthesis of azole nucleoside analogues of d-pinitol as potential antitumor agents

  摘要：

  A convenient strategy is reported for the synthesis of azole nucleoside analogues of D-pinitol (=3-O-methyl-D-chiro-inositol). The key intermediate 3-O-methyl-4,5-epoxy-D-chiro-inositol was obtained in excellent yield via an epoxidation from monomethanesulfonate Of D-pinitol. The process of opening of the epoxy ring by azole-bases appeared strongly regioselective in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene. All newly synthesized carbocyclic azole nucleosides were assayed against lung and bladder cancer in vitro. Only the triazole and benzotriazole nucleoside analogues inhibited the growth of human lung cancer cell lines (PG) with EC(50) of 11.3 and 22.6 mu M, respectively, and showed much less inhibitory activity against human bladder cell lines (T(24)). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.01.004