ethyl (1R,5R,6S)-<3-(tert-butyldimethylsiloxy)-5,6-O-isopropylidene-5,6-dihydroxy-2-cyclohexen-1-yl>acetate | 130097-07-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (1R,5R,6S)-<3-(tert-butyldimethylsiloxy)-5,6-O-isopropylidene-5,6-dihydroxy-2-cyclohexen-1-yl>acetate
• 英文别名: ethyl 2-[(3aS,4R,7aR)-6-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxol-4-yl]acetate
• CAS: 130097-07-3
• 化学式: C₁₉H₃₄O₅Si
• 分子量: 370.561
• InChiKey: DNGBVEYJWKQSSX-LXZKKBNFSA-N

物化性质

• 沸点：
  389.4±42.0 °C(predicted)
• 密度：
  1.03±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (1R,5R,6S)-<3-(tert-butyldimethylsiloxy)-5,6-O-isopropylidene-5,6-dihydroxy-2-cyclohexen-1-yl>acetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.08h， 生成
  参考文献：
  名称：

  Total Synthesis of (+)-Cryptocaryanone A

  摘要：

  The first total synthesis of (+)-cryptocaryanone A is described. The synthesis features a Mukaiyama aldol reaction, one-pot saponification/lactonization sequences, and TsOH-assisted dihydropyrone formation as key steps.

  DOI：

  10.1055/s-0032-1316580
• 作为产物：
  描述：

  1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene 、 (4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one 在 mercury(II) iodide 作用下， 以 乙醚 为溶剂， 以90%的产率得到ethyl (1R,5R,6S)-<3-(tert-butyldimethylsiloxy)-5,6-O-isopropylidene-5,6-dihydroxy-2-cyclohexen-1-yl>acetate
  参考文献：
  名称：

  Total Synthesis of (+)-Cryptocaryanone A

  摘要：

  The first total synthesis of (+)-cryptocaryanone A is described. The synthesis features a Mukaiyama aldol reaction, one-pot saponification/lactonization sequences, and TsOH-assisted dihydropyrone formation as key steps.

  DOI：

  10.1055/s-0032-1316580

文献信息

• On the diastereofacial selectivity of Lewis acid-catalyzed carbon-carbon bond forming reactions of conjugated cyclic enones bearing electron-withdrawing substituents at the .gamma.-position
  作者：Lucio O. Jeroncic、Maria Paz Cabal、Samuel J. Danishefsky、Gayle M. Shulte

  DOI：10.1021/jo00001a070

  日期：1991.1

  Lewis acid catalyzed reactions of several cyclic enones are described. The gamma-OTBS enones 1 and 2 give products where carbon-carbon bond formation at the beta carbon occurs with high stereoselectivity favoring attack syn to the resident OTBS group. In the case of enone 24 bearing an additional dioxolane ring, the products correspond to addition anti to the resident carbon-oxygen bond at the gamma carbon. The reaction of 24 with lithium dimethylcuprate also occurs in an anti sense. The starting materials in this study are available in quantity in optically pure form. Given the excellent stereoselectivity of the reactions, these compounds are useful intermediates for synthesis.
• JERONCIC, LUCIO O.;CABAL, MARIA-PAZ;DANISHEFSKY, SAMUEL J.;SHULTE, GAYLE +, J. ORG. CHEM., 56,(1991) N, C. 387-395
  作者：JERONCIC, LUCIO O.、CABAL, MARIA-PAZ、DANISHEFSKY, SAMUEL J.、SHULTE, GAYLE +

  DOI：——

  日期：——
• Total Synthesis of (+)-Cryptocaryanone A
  作者：Xingang Xie、Xuegong She、Bingbin Zhang、Zhen Yang、Juan Yang、Gaoyuan Zhao、Bin Ma

  DOI：10.1055/s-0032-1316580

  日期：2012.9

  The first total synthesis of (+)-cryptocaryanone A is described. The synthesis features a Mukaiyama aldol reaction, one-pot saponification/lactonization sequences, and TsOH-assisted dihydropyrone formation as key steps.