(1R,2R,3R,6S,7S,7aR)-1,2,7-tris(benzyloxy)-3-[(benzyloxy)methyl]hexahydro-1H-pyrrolizin-6-ol | 1194242-42-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R,3R,6S,7S,7aR)-1,2,7-tris(benzyloxy)-3-[(benzyloxy)methyl]hexahydro-1H-pyrrolizin-6-ol
• 英文别名: (1S,2R,5R,6R,7R,8R)-1,6,7-tris(phenylmethoxy)-5-(phenylmethoxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-2-ol
• CAS: 1194242-42-6
• 化学式: C₃₆H₃₉NO₅
• 分子量: 565.709
• InChiKey: AYJSRLUKGJDVOC-HLPCWDLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,6S,7S,7aR)-1,2,7-tris(benzyloxy)-3-[(benzyloxy)methyl]hexahydro-1H-pyrrolizin-6-ol 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 96.0h， 以71%的产率得到6-epi-casuarine
  参考文献：
  名称：

  Total Synthesis of (−)-Uniflorine A

  摘要：

  Total synthesis of (-)-uniflorine A (3) has been accomplished in nine steps and 11% overall yield from carbohydrate-based nitrone 5. The key steps of the synthetic strategy were a high regio- and complete stereoselective 1,3-dipolar cycloaddition of alkene 6 with nitrone 5, a Tamao-Fleming reaction for replacing the silicon substituent with a hydroxy group with retention of configuration, and a Mitsunobu reaction to establish the correct configuration of the target molecule at C-6.

  DOI：

  10.1021/np900435d
• 作为产物：
  描述：

  (1R,2R,3R,6S,7S,7aS)-1,2,7-tris(benzyloxy)-3-[(benzyloxy)methyl]-5-oxo-hexahydro-5H-pyrrolizin-6-yl benzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以45%的产率得到(1R,2R,3R,6S,7S,7aR)-1,2,7-tris(benzyloxy)-3-[(benzyloxy)methyl]hexahydro-1H-pyrrolizin-6-ol
  参考文献：
  名称：

  Total Synthesis of (−)-Uniflorine A

  摘要：

  Total synthesis of (-)-uniflorine A (3) has been accomplished in nine steps and 11% overall yield from carbohydrate-based nitrone 5. The key steps of the synthetic strategy were a high regio- and complete stereoselective 1,3-dipolar cycloaddition of alkene 6 with nitrone 5, a Tamao-Fleming reaction for replacing the silicon substituent with a hydroxy group with retention of configuration, and a Mitsunobu reaction to establish the correct configuration of the target molecule at C-6.

  DOI：

  10.1021/np900435d

文献信息

• Total Synthesis of (−)-Uniflorine A
  作者：Camilla Parmeggiani、Daniele Martella、Francesca Cardona、Andrea Goti

  DOI：10.1021/np900435d

  日期：2009.11.30

  Total synthesis of (-)-uniflorine A (3) has been accomplished in nine steps and 11% overall yield from carbohydrate-based nitrone 5. The key steps of the synthetic strategy were a high regio- and complete stereoselective 1,3-dipolar cycloaddition of alkene 6 with nitrone 5, a Tamao-Fleming reaction for replacing the silicon substituent with a hydroxy group with retention of configuration, and a Mitsunobu reaction to establish the correct configuration of the target molecule at C-6.