[(3aR,4R,9R,9aR,9bS)-9-(methoxymethoxy)spiro[3a,4,6,7,8,9,9a,9b-octahydro-[1,3]dioxolo[4,5-a]indolizine-2,1'-cyclohexane]-4-yl]methanol | 389797-52-8

• 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: [(3aR,4R,9R,9aR,9bS)-9-(methoxymethoxy)spiro[3a,4,6,7,8,9,9a,9b-octahydro-[1,3]dioxolo[4,5-a]indolizine-2,1'-cyclohexane]-4-yl]methanol
• CAS: 389797-52-8
• 化学式: C₁₇H₂₉NO₅
• 分子量: 327.421
• InChiKey: WHOCFSBOOATJIO-QCODTGAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3aR,4R,9R,9aR,9bS)-9-(methoxymethoxy)spiro[3a,4,6,7,8,9,9a,9b-octahydro-[1,3]dioxolo[4,5-a]indolizine-2,1'-cyclohexane]-4-yl]methanol 在 盐酸 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,2R,3R,8R,8aR)-3-[(4-phenylphenyl)methoxymethyl]-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 作用下， 以 四氢呋喃 为溶剂， 生成 [(3aR,4R,9R,9aR,9bS)-9-(methoxymethoxy)spiro[3a,4,6,7,8,9,9a,9b-octahydro-[1,3]dioxolo[4,5-a]indolizine-2,1'-cyclohexane]-4-yl]methanol
  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

• Preparation of immobilized swainsonine analogs on solid support
  作者：William H Pearson、Luyi Guo、Tanya M Jewell

  DOI：10.1016/s0040-4039(02)00254-x

  日期：2002.3

  Golgi alpha-mannosidase II and lysosomal mannosidase are examples of biologically important alpha-mannosidases that are difficult to purify. Swainsonine is an effective inhibitor of these a-mannosidases. In this report, analogs of swainsonine bearing an aminoalkyl group at C3 or C6 are synthesized and coupled with AM-Gel 10 to prepare affinity matrices that may be useful for the preparation of alpha-mannosidases. Model ligands, where the aminoalkyl group is capped with an acyl group, are evaluated against a commercial alpha-mannosidase. (C) 2002 Elsevier Science Ltd. All rights reserved.