(1S,5S,6R)-2-allyl-6-(tert-butyldimethylsilyloxy)-1-vinyl-2-azaspiro{bicyclo[3.3.1]nonane-4,2′-[1,3]dioxolane} | 1416404-25-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (1S,5S,6R)-2-allyl-6-(tert-butyldimethylsilyloxy)-1-vinyl-2-azaspiro{bicyclo[3.3.1]nonane-4,2′-[1,3]dioxolane}
• 英文别名: tert-butyl-[(1'S,5'S,6'R)-1'-ethenyl-2'-prop-2-enylspiro[1,3-dioxolane-2,4'-2-azabicyclo[3.3.1]nonane]-6'-yl]oxy-dimethylsilane
• CAS: 1416404-25-5
• 化学式: C₂₁H₃₇NO₃Si
• 分子量: 379.615
• InChiKey: MVHROPZOOWMNKU-NSHGMRRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,5S,6R)-2-allyl-6-(tert-butyldimethylsilyloxy)-1-vinyl-2-azaspiro{bicyclo[3.3.1]nonane-4,2′-[1,3]dioxolane} 在 对甲苯磺酸 作用下， 以 水 、 丙酮 为溶剂， 反应 6.0h， 以76%的产率得到(1S,5S,6R)-2-allyl-1-vinyl-2-azaspiro[bicyclo[3.3.1]nonane-4,2'-[1,3]dioxolan]-6-ol
  参考文献：
  名称：

  Enantioselective Total Syntheses of (−)-FR901483 and (+)-8-epi-FR901483

  摘要：

  The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diaster-eoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.

  DOI：

  10.1021/jo302362b
• 作为产物：
  描述：

  (R)-1-allyl-5-(benzyloxy)piperidin-2-one 在 盐酸 、 2,6-二叔丁基-4-甲基吡啶 、 草酰氯 、 三氟甲磺酸酐 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.67h， 生成 (1S,5S,6R)-2-allyl-6-(tert-butyldimethylsilyloxy)-1-vinyl-2-azaspiro{bicyclo[3.3.1]nonane-4,2′-[1,3]dioxolane}
  参考文献：
  名称：

  Enantioselective Total Syntheses of (−)-FR901483 and (+)-8-epi-FR901483

  摘要：

  The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diaster-eoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.

  DOI：

  10.1021/jo302362b

文献信息

• Enantioselective Total Syntheses of (−)-FR901483 and (+)-8-<i>epi</i>-FR901483
  作者：Hao-Hua Huo、Xiao-Er Xia、Hong-Kui Zhang、Pei-Qiang Huang

  DOI：10.1021/jo302362b

  日期：2013.1.18

  The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diaster-eoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.