(3aR,5R,6S,6aR)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-nonoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5R,6S,6aR)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-nonoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• 化学式: C₂₁H₃₈O₆
• 分子量: 386.529
• InChiKey: RBBZSIFZZRPZPJ-ZWJWXYIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6S,6aR)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-nonoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole 在 氢气 作用下， 生成 (3R,4S,5R,6R)-6-(hydroxymethyl)-4-(nonyloxy)-tetrahydro-2H-pyran-2,3,5-triol
  参考文献：
  名称：

  Probing structure/affinity relationships for the Plasmodium falciparum hexose transporter with glucose derivatives

  摘要：

  A series of 3-O-substituted glucose derivatives was prepared with alkyl, alkenyl, aromatic and ferrocenic substituents; to vary lipophilicity and hydrogen bonding ethylenedioxy and perfluorinated fragments were also introduced. Apparent affinities for the Plasmodium falciparum hexose transporter (PfHT) were determined after heterologous expression in Xenopus oocytes, with highest affinities for compounds with C8-C13 lipophilic chains. As no derivatives show significant affinity for the mammalian glucose transporter (GLUT1), these structure/affinity assays contribute to design of potent PfHT inhibitors and eventual development of antimalarials. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.068
• 作为产物：
  描述：

  1,2:5,6-diacetone-D-glucose 、 1-溴壬烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (3aR,5R,6S,6aR)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-nonoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
  参考文献：
  名称：

  Probing structure/affinity relationships for the Plasmodium falciparum hexose transporter with glucose derivatives

  摘要：

  A series of 3-O-substituted glucose derivatives was prepared with alkyl, alkenyl, aromatic and ferrocenic substituents; to vary lipophilicity and hydrogen bonding ethylenedioxy and perfluorinated fragments were also introduced. Apparent affinities for the Plasmodium falciparum hexose transporter (PfHT) were determined after heterologous expression in Xenopus oocytes, with highest affinities for compounds with C8-C13 lipophilic chains. As no derivatives show significant affinity for the mammalian glucose transporter (GLUT1), these structure/affinity assays contribute to design of potent PfHT inhibitors and eventual development of antimalarials. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.068