(3aR,7S,9R,9aS,9bS)-9-[tert-butyl(dimethyl)silyl]oxy-7-(4-chlorobutyl)-2,2-dimethyl-4,7,8,9,9a,9b-hexahydro-3aH-[1,3]dioxolo[4,5-a]indolizin-6-one | 433926-64-8

• 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,7S,9R,9aS,9bS)-9-[tert-butyl(dimethyl)silyl]oxy-7-(4-chlorobutyl)-2,2-dimethyl-4,7,8,9,9a,9b-hexahydro-3aH-[1,3]dioxolo[4,5-a]indolizin-6-one
• CAS: 433926-64-8
• 化学式: C₂₁H₃₈ClNO₄Si
• 分子量: 432.076
• InChiKey: SPKRPGSOLVILDS-YYWYGQEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,7S,9R,9aS,9bS)-9-[tert-butyl(dimethyl)silyl]oxy-7-(4-chlorobutyl)-2,2-dimethyl-4,7,8,9,9a,9b-hexahydro-3aH-[1,3]dioxolo[4,5-a]indolizin-6-one 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 以98%的产率得到(3aR,7S,9R,9aS,9bS)-7-(4-Azido-butyl)-9-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-a]indolizin-6-one
  参考文献：
  名称：

  Preparation of immobilized swainsonine analogs on solid support

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(02)00254-x
• 作为产物：
  描述：

  (1S,2R,8R,8aR)-8-hydroxy-1,2-(isopropylidenedioxy)octahydroindolizin-5-one 在 咪唑 、 仲丁基锂 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (3aR,7S,9R,9aS,9bS)-9-[tert-butyl(dimethyl)silyl]oxy-7-(4-chlorobutyl)-2,2-dimethyl-4,7,8,9,9a,9b-hexahydro-3aH-[1,3]dioxolo[4,5-a]indolizin-6-one
  参考文献：
  名称：

  Preparation of immobilized swainsonine analogs on solid support

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(02)00254-x

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.