(3aR,4R,9R,9aR,9bS)-9-(methoxymethoxy)-4-(phenylmethoxymethyl)spiro[3a,4,6,7,8,9,9a,9b-octahydro-[1,3]dioxolo[4,5-a]indolizine-2,1'-cyclohexane] | 389797-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (3aR,4R,9R,9aR,9bS)-9-(methoxymethoxy)-4-(phenylmethoxymethyl)spiro[3a,4,6,7,8,9,9a,9b-octahydro-[1,3]dioxolo[4,5-a]indolizine-2,1'-cyclohexane]
• CAS: 389797-54-0
• 化学式: C₂₄H₃₅NO₅
• 分子量: 417.546
• InChiKey: DAKUKNKDUUVVJK-JLMDMGSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,4R,9R,9aR,9bS)-9-(methoxymethoxy)-4-(phenylmethoxymethyl)spiro[3a,4,6,7,8,9,9a,9b-octahydro-[1,3]dioxolo[4,5-a]indolizine-2,1'-cyclohexane] 在 盐酸 、 Dowex 1X₈-200 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到(1S,2R,3R,8R,8aR)-3-(phenylmethoxymethyl)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,2,8-triol
  参考文献：
  名称：

  Synthesis and mannosidase inhibitory activity of 3-benzyloxymethyl analogs of swainsonine

  摘要：

  Swainsonine (3), an inhibitor of Golgi alpha -mannosidase II, is a clinical candidate for cancer treatment. In order to avoid potential problems arising from its co-inhibition of lysosomal mannosidases, we have synthesized 3-benzyloxymethyl analogs of swainsonine (17 and 18). Initial screening of these new compounds is reported. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)01777-4
• 作为产物：
  描述：

  (3aR,4R,9R,9aR,9bS)-4-(hydroxymethyl)-9-(methoxymethoxy)spiro[4,7,8,9,9a,9b-hexahydro-3aH-[1,3]dioxolo[4,5-a]indolizine-2,1'-cyclohexane]-6-one 在 dimethyl sulfide borane 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (3aR,4R,9R,9aR,9bS)-9-(methoxymethoxy)-4-(phenylmethoxymethyl)spiro[3a,4,6,7,8,9,9a,9b-octahydro-[1,3]dioxolo[4,5-a]indolizine-2,1'-cyclohexane]
  参考文献：
  名称：

  Synthesis and mannosidase inhibitory activity of 3-benzyloxymethyl analogs of swainsonine

  摘要：

  Swainsonine (3), an inhibitor of Golgi alpha -mannosidase II, is a clinical candidate for cancer treatment. In order to avoid potential problems arising from its co-inhibition of lysosomal mannosidases, we have synthesized 3-benzyloxymethyl analogs of swainsonine (17 and 18). Initial screening of these new compounds is reported. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)01777-4

文献信息

• Synthesis and mannosidase inhibitory activity of 3-benzyloxymethyl analogs of swainsonine
  作者：William H Pearson、Luyi Guo

  DOI：10.1016/s0040-4039(01)01777-4

  日期：2001.11

  Swainsonine (3), an inhibitor of Golgi alpha -mannosidase II, is a clinical candidate for cancer treatment. In order to avoid potential problems arising from its co-inhibition of lysosomal mannosidases, we have synthesized 3-benzyloxymethyl analogs of swainsonine (17 and 18). Initial screening of these new compounds is reported. (C) 2001 Published by Elsevier Science Ltd.