tert-butyl [(Z,4S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxybut-2-enyl] carbonate | 790300-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl [(Z,4S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxybut-2-enyl] carbonate
• CAS: 790300-39-9
• 化学式: C₁₄H₂₄O₆
• 分子量: 288.341
• InChiKey: MPQZKSKHXZTHJM-QIAMSNJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl [(Z,4S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxybut-2-enyl] carbonate 在 四(三苯基膦)钯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以61%的产率得到1H-嘌呤-2-胺,6,9-二氢-6-亚氨基-N,N,1,9-四甲基-
  参考文献：
  名称：

  An Efficient, Stereoselective Approach to syn-1,2-Diols Protected as Cyclic Carbonates

  摘要：

  Enantioenriched 4-hydroxyalk-2-ynyl carbonates (or benzoates) have been prepared by stereoselective zinc-mediated addition of alkyl 2-propynyl carbonates (or their benzoate analogues) to aldehydes. Their partial reduction to Z-olefins followed by cyclization under mild Pd-catalyzed conditions allowed a straightforward access to enantioenriched syn-1,2-diols protected as cyclic carbonates.

  DOI：

  10.1021/jo048985g
• 作为产物：
  描述：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 Lindlar's catalyst 喹啉 、 氢气 、 zinc trifluoromethanesulfonate 、 (+)-N-methylephedrine 、 三乙胺 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 3.25h， 生成 tert-butyl [(Z,4S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxybut-2-enyl] carbonate
  参考文献：
  名称：

  An Efficient, Stereoselective Approach to syn-1,2-Diols Protected as Cyclic Carbonates

  摘要：

  Enantioenriched 4-hydroxyalk-2-ynyl carbonates (or benzoates) have been prepared by stereoselective zinc-mediated addition of alkyl 2-propynyl carbonates (or their benzoate analogues) to aldehydes. Their partial reduction to Z-olefins followed by cyclization under mild Pd-catalyzed conditions allowed a straightforward access to enantioenriched syn-1,2-diols protected as cyclic carbonates.

  DOI：

  10.1021/jo048985g

文献信息

• An Efficient, Stereoselective Approach to <i>s</i><i>yn</i>-1,2-Diols Protected as Cyclic Carbonates
  作者：Yohan Georges、Yves Allenbach、Xavier Ariza、Jean-Marc Campagne、Jordi Garcia

  DOI：10.1021/jo048985g

  日期：2004.10.1

  Enantioenriched 4-hydroxyalk-2-ynyl carbonates (or benzoates) have been prepared by stereoselective zinc-mediated addition of alkyl 2-propynyl carbonates (or their benzoate analogues) to aldehydes. Their partial reduction to Z-olefins followed by cyclization under mild Pd-catalyzed conditions allowed a straightforward access to enantioenriched syn-1,2-diols protected as cyclic carbonates.