ethyl (4S)-4-[(4R,5S)-5-[(R)-[tert-butyl(dimethyl)silyl]oxy-phenylmethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(E)-3-phenylprop-2-enoyl]oxybut-2-ynoate | 1211548-20-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (4S)-4-[(4R,5S)-5-[(R)-[tert-butyl(dimethyl)silyl]oxy-phenylmethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(E)-3-phenylprop-2-enoyl]oxybut-2-ynoate
• CAS: 1211548-20-7
• 化学式: C₃₃H₄₂O₇Si
• 分子量: 578.778
• InChiKey: ZKCDWBYZGQONMF-QZFJAQMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.46
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl (4S)-4-[(4R,5S)-5-[(R)-[tert-butyl(dimethyl)silyl]oxy-phenylmethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(E)-3-phenylprop-2-enoyl]oxybut-2-ynoate 在 喹啉 、 氢气 作用下， 以 正己烷 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 以90%的产率得到
  参考文献：
  名称：

  First total synthesis of (+)-crassalactone A

  摘要：

  A simple and highly efficient first total synthesis Of cytotoxic (+)-crassalactone A starting from (R)-mandelic acid is described. The strategy involves the osmium tetroxide-catalyzed cis-hydroxylation and the stereoselective addition of ethyl lithiopropiolate to a chiral aldehyde intermediate as key steps. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.038
• 作为产物：
  描述：

  肉桂酸 、 ethyl 7S-t-butyldimethylsilyloxy-7-phenyl-5S,6S-O-isopropylidene-4S-hydroxy-heptyn-2-oate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以65%的产率得到ethyl (4S)-4-[(4R,5S)-5-[(R)-[tert-butyl(dimethyl)silyl]oxy-phenylmethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(E)-3-phenylprop-2-enoyl]oxybut-2-ynoate
  参考文献：
  名称：

  First total synthesis of (+)-crassalactone A

  摘要：

  A simple and highly efficient first total synthesis Of cytotoxic (+)-crassalactone A starting from (R)-mandelic acid is described. The strategy involves the osmium tetroxide-catalyzed cis-hydroxylation and the stereoselective addition of ethyl lithiopropiolate to a chiral aldehyde intermediate as key steps. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.038

文献信息

• First total synthesis of (+)-crassalactone A
  作者：V. Shekhar、D. Kumar Reddy、V. Suresh、D. Chanti Babu、Y. Venkateswarlu

  DOI：10.1016/j.tetlet.2009.12.038

  日期：2010.2

  A simple and highly efficient first total synthesis Of cytotoxic (+)-crassalactone A starting from (R)-mandelic acid is described. The strategy involves the osmium tetroxide-catalyzed cis-hydroxylation and the stereoselective addition of ethyl lithiopropiolate to a chiral aldehyde intermediate as key steps. (C) 2009 Elsevier Ltd. All rights reserved.