(3aS,8aR,9aS)-2,2-dimethyl-9-methylene-octahydro[1,3]dioxolo[4,5-f]indolizine | 942996-83-0

• 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: (3aS,8aR,9aS)-2,2-dimethyl-9-methylene-octahydro[1,3]dioxolo[4,5-f]indolizine
• 英文别名: (3aS,8aR,9aS)-2,2-dimethyl-9-methylidene-4,6,7,8,8a,9a-hexahydro-3aH-[1,3]dioxolo[4,5-f]indolizine
• CAS: 942996-83-0
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: VHWMTACDKPMCRX-VWYCJHECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,8aR,9aS)-2,2-dimethyl-9-methylene-octahydro[1,3]dioxolo[4,5-f]indolizine 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 叠氮化锂 、 氢气 、 silica gel 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 49.17h， 生成 (6S,7S,8R,8aR)-8-amino-octahydroindolizine-6,7-diol
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tet.2007.03.085
• 作为产物：
  描述：

  (4R,5S)-5-Ethynyl-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 在 萘-1,4-二腈 、 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 、 异丙醇 为溶剂， 反应 8.5h， 生成 (3aS,8aR,9aS)-2,2-dimethyl-9-methylene-octahydro[1,3]dioxolo[4,5-f]indolizine
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tet.2007.03.085

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.