ethyl (2R,3R)-3-(6-bromo-1,3-benzodioxol-5-yl)-4-[ (tert-butyldimethylsilyl)oxy]-2-[(3,4,5-trimethoxyphenyl)amino]butanoate | 1448019-83-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (2R,3R)-3-(6-bromo-1,3-benzodioxol-5-yl)-4-[ (tert-butyldimethylsilyl)oxy]-2-[(3,4,5-trimethoxyphenyl)amino]butanoate
• 英文别名: ethyl (2R,3R)-3-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-4-[tert-butyl(dimethyl)silyl]oxy-2-(3,4,5-trimethoxyanilino)butanoate
• CAS: 1448019-83-7
• 化学式: C₂₉H₄₂BrNO₈Si
• 分子量: 640.644
• InChiKey: XZCBRDQHZWICSU-AFMDSPMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3,4-methylenedioxy-trans-cinnamic acid 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 草酰氯 、 硫酸 、 palladium 10% on activated carbon 、 氢气 、 溴 、 二甲基亚砜 、 D-脯氨酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、379.22 kPa 条件下， 反应 44.75h， 生成 ethyl (2R,3R)-3-(6-bromo-1,3-benzodioxol-5-yl)-4-[ (tert-butyldimethylsilyl)oxy]-2-[(3,4,5-trimethoxyphenyl)amino]butanoate 、 ethyl anti-3-(6-bromo-1,3-benzodioxol-5-yl)-4-[ (tert-butyldimethylsilyl)oxy]-2-[(3,4,5-trimethoxyphenyl)amino]butanoate
  参考文献：
  名称：

  Asymmetric Synthesis of 1-Aza-4-deoxypicropodophyllotoxin

  摘要：

  In our search for new easily accessible analogues based on the natural product podophyllotoxin, we synthesized 1-aza-4-deoxypicropodophyllotoxin in good overall yield and excellent enantioselectivity. The synthesis was centered around a direct asymmetric Mannich reaction using D-proline as the key step for introduction of the chiral centres. Our synthesis of 1-aza-4-deoxypodophyllotoxin was hindered through the increased instability towards epimerization of the C2 position. We did, however, synthesized a new scaffold based on the opened lactone analogue.

  DOI：

  10.1055/s-0033-1338414

文献信息

• Asymmetric Synthesis of 1-Aza-4-deoxypicropodophyllotoxin
  作者：Wim De Borggraeve、Benoit Aigret、Jeroen Jacobs、Luc Van Meervelt

  DOI：10.1055/s-0033-1338414

  日期：——

  In our search for new easily accessible analogues based on the natural product podophyllotoxin, we synthesized 1-aza-4-deoxypicropodophyllotoxin in good overall yield and excellent enantioselectivity. The synthesis was centered around a direct asymmetric Mannich reaction using D-proline as the key step for introduction of the chiral centres. Our synthesis of 1-aza-4-deoxypodophyllotoxin was hindered through the increased instability towards epimerization of the C2 position. We did, however, synthesized a new scaffold based on the opened lactone analogue.