tert-butyl ((2R,3R,E)-3-((tert-butyldimethylsilyl)oxy)-1-(2-oxodihydrofuran-3(2H)-ylidene)butan-2-yl)carbamate | 1416253-53-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: tert-butyl ((2R,3R,E)-3-((tert-butyldimethylsilyl)oxy)-1-(2-oxodihydrofuran-3(2H)-ylidene)butan-2-yl)carbamate
• 英文别名: tert-butyl N-[(1E,2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-1-(2-oxooxolan-3-ylidene)butan-2-yl]carbamate
• CAS: 1416253-53-6
• 化学式: C₁₉H₃₅NO₅Si
• 分子量: 385.576
• InChiKey: WRUZRQHWMFCRQK-CNNVDREISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl ((2R,3R,E)-3-((tert-butyldimethylsilyl)oxy)-1-(2-oxodihydrofuran-3(2H)-ylidene)butan-2-yl)carbamate 在 盐酸 、 间氯过氧苯甲酸 、 三氟乙酸 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 6.33h， 生成 (S)-3-hydroxy-3-((R,E)-3-hydroxybut-1-en-1-yl)-dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Construction of Chiral Tertiary Alcohol Stereocenters via the [2,3]- Meisenheimer Rearrangement: Enantioselective Synthesis of the Side-Chain Acids of Homoharringtonine and Harringtonine

  摘要：

  For the first time, the [2,3]-Meisenheimer rearrangement has been developed into a general strategy for the construction of chiral tertiary alcohols. The effectiveness and practicality of this methodology are illustrated by the successful synthesis of (R)-20 and (R)-30, the side chain acids of homoharringtonine and harringtonine, respectively.

  DOI：

  10.1021/jo302203g
• 作为产物：
  描述：

  二氢-3-(三苯基膦亚基)-2(3H)-呋喃酮 、 (2R,3R)-2-(tert-butoxycarbonylamino)-3-O-(tert-butyldimethylsilyl)-1,3-butanediol 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到tert-butyl ((2R,3R,E)-3-((tert-butyldimethylsilyl)oxy)-1-(2-oxodihydrofuran-3(2H)-ylidene)butan-2-yl)carbamate
  参考文献：
  名称：

  Construction of Chiral Tertiary Alcohol Stereocenters via the [2,3]- Meisenheimer Rearrangement: Enantioselective Synthesis of the Side-Chain Acids of Homoharringtonine and Harringtonine

  摘要：

  For the first time, the [2,3]-Meisenheimer rearrangement has been developed into a general strategy for the construction of chiral tertiary alcohols. The effectiveness and practicality of this methodology are illustrated by the successful synthesis of (R)-20 and (R)-30, the side chain acids of homoharringtonine and harringtonine, respectively.

  DOI：

  10.1021/jo302203g

文献信息

• Construction of Chiral Tertiary Alcohol Stereocenters via the [2,3]- Meisenheimer Rearrangement: Enantioselective Synthesis of the Side-Chain Acids of Homoharringtonine and Harringtonine
  作者：Hua Yang、Moran Sun、Shuguang Zhao、Ming Zhu、Yangla Xie、Changling Niu、Chunlin Li

  DOI：10.1021/jo302203g

  日期：2013.1.18

  For the first time, the [2,3]-Meisenheimer rearrangement has been developed into a general strategy for the construction of chiral tertiary alcohols. The effectiveness and practicality of this methodology are illustrated by the successful synthesis of (R)-20 and (R)-30, the side chain acids of homoharringtonine and harringtonine, respectively.