(3aS,8aR,9S,9aS)-2,2-dimethyl-octahydro[1,3]dioxolo[4,5-f]indolizin-9-ol | 214400-47-2

• 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: (3aS,8aR,9S,9aS)-2,2-dimethyl-octahydro[1,3]dioxolo[4,5-f]indolizin-9-ol
• 英文别名: (3aS,8aR,9S,9aS)-2,2-dimethyl-3a,4,6,7,8,8a,9,9a-octahydro-[1,3]dioxolo[4,5-f]indolizin-9-ol
• CAS: 214400-47-2
• 化学式: C₁₁H₁₉NO₃
• 分子量: 213.277
• InChiKey: MUSBUHVMKWYQIF-XFWSIPNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aS,8aR,9S,9aS)-2,2-dimethyl-octahydro[1,3]dioxolo[4,5-f]indolizin-9-ol 在 三氟乙酸 作用下， 以91%的产率得到1-deoxy-8-epi-castanospermine
  参考文献：
  名称：

  Stereoselective synthesis of hydroxyindolizidines via sparteine-assisted deprotonation of N-Boc-pyrrolidine

  摘要：

  Three diastereoisomers of 1-deoxycastanospermine were synthesized in enantiomerically pure form. The key step in the synthesis involved reaction of lithiated N-Boc-pyrrolidine in the presence of sparteine with a chiral building block derived from tartaric acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01491-9
• 作为产物：
  描述：

  (4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde 在 palladium on activated charcoal 四氯化碳 、 sodium hydroxide 、 氢气 、 仲丁基锂 、 sodium hydride 、 potassium carbonate 、 三苯基膦 、 鹰爪豆碱 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.25h， 生成 (3aS,8aR,9S,9aS)-2,2-dimethyl-octahydro[1,3]dioxolo[4,5-f]indolizin-9-ol
  参考文献：
  名称：

  Stereoselective synthesis of hydroxyindolizidines via sparteine-assisted deprotonation of N-Boc-pyrrolidine

  摘要：

  Three diastereoisomers of 1-deoxycastanospermine were synthesized in enantiomerically pure form. The key step in the synthesis involved reaction of lithiated N-Boc-pyrrolidine in the presence of sparteine with a chiral building block derived from tartaric acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01491-9

文献信息

• Synthesis and evaluation of 1-deoxy-8-epi-castanospermine, 1-deoxy-8-hydroxymethyl castanospermine, and (6S,7S,8R,8aR)-8-amino-octahydroindolizine-6,7-diol
  作者：Ganesh Pandey、Shrinivas G. Dumbre、Sujit Pal、M. Islam Khan、M. Shabab

  DOI：10.1016/j.tet.2007.03.085

  日期：2007.5

  A short, versatile, and enantioselective synthesis of 1-deoxy-8-epi-castanospermine (5), 1-deoxy-8-hydroxymethyl castanospermine (6), and (6S,7S,8R,8aR)-8-amino-octahydroindolizine-6,7-diol (7) is achieved from a common template 12. The key step utilized is PET provoked amine radical cyclization of 11 to 12 in excellent diastereoselectivity. The exocyclic double bond at C-8 of the template is functionalized to obtain 5-7 as exclusive diastereomers. 1-Deoxy-8-epi-castanospermine exhibited inhibition of alpha- and beta-galactosidase and beta-glucosidase. Compounds 6 and 7 were found to be weak inhibitors of beta-glucosidase. (C) 2007 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of hydroxyindolizidines via sparteine-assisted deprotonation of N-Boc-pyrrolidine
  作者：Marek Majewski、Jianxing Shao、Ken Nelson、Pawel Nowak、Nicholas M. Irvine

  DOI：10.1016/s0040-4039(98)01491-9

  日期：1998.9

  Three diastereoisomers of 1-deoxycastanospermine were synthesized in enantiomerically pure form. The key step in the synthesis involved reaction of lithiated N-Boc-pyrrolidine in the presence of sparteine with a chiral building block derived from tartaric acid. (C) 1998 Elsevier Science Ltd. All rights reserved.