1-{[(4S,5S)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-2-(trimethylsilyl)pyrrolidine | 942996-82-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-{[(4S,5S)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-2-(trimethylsilyl)pyrrolidine
• 英文别名: [1-[[(4S,5S)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]pyrrolidin-2-yl]-trimethylsilane
• CAS: 942996-82-9
• 化学式: C₁₅H₂₇NO₂Si
• 分子量: 281.47
• InChiKey: DQZCKZRVVCDXTN-RFHHWMCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 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：

  1-{[(4S,5S)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-2-(trimethylsilyl)pyrrolidine 在 sodium periodate 、 四氧化锇 、 萘-1,4-二腈 、 silica gel 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 异丙醇 、 叔丁醇 为溶剂， 反应 12.67h， 生成
  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 、 2-(Trimethylsilyl)pyrrolidine 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 8.0h， 以73%的产率得到1-{[(4S,5S)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-2-(trimethylsilyl)pyrrolidine
  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