[(4S)-5-oxo-4-tri(propan-2-yl)silyloxypentyl] 2,2-dimethylpropanoate | 180923-36-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(4S)-5-oxo-4-tri(propan-2-yl)silyloxypentyl] 2,2-dimethylpropanoate
• CAS: 180923-36-8
• 化学式: C₁₉H₃₈O₄Si
• 分子量: 358.594
• InChiKey: CZINZKHCKZRSSF-KRWDZBQOSA-N

物化性质

• 沸点：
  390.6±37.0 °C(Predicted)
• 密度：
  0.927±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(4S)-5-oxo-4-tri(propan-2-yl)silyloxypentyl] 2,2-dimethylpropanoate 在 titanium(IV) isopropylate 、 sodium cyanoborohydride 作用下， 以 乙醇 为溶剂， 反应 16.5h， 生成
  参考文献：
  名称：

  Catalytic asymmetric synthesis of protected α-hydroxy aldehydes and related 1,2-difunctional chiral building blocks. An enantioselective synthesis of (−)-exo- and (−)-endo-brevicomin

  摘要：

  Chiral allylic alcohols which were prepared by the addition of functionalized dialkylzincs to alpha,beta-unsaturated aldehydes in good to excellent enantioselectivity, were converted to protected alpha-hydroxy aldehydes and 1,2-amino alcohols without loss of enantiomeric purity. Syn- or anti-1,2-diols can be obtained stereoselectively by a second asymmetric addition to alpha-silyloxy aldehydes. Functionalized 1,2-diols prepared in this way were converted to enantiomerically pure (-)-exo- and (-)-endo-brevicomin (>99% ee). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00036-0
• 作为产物：
  描述：

  di(3-pivaloyloxypropyl)zinc 在 三乙烯二胺 、 咪唑 、 titanium(IV) isopropylate 、 sodium periodate 、 potassium dioxotetrahydroxoosmate(VI) 、 potassium carbonate 、 (1R)-反-N,N′-1,2-环己二基双(1,1,1-三氟甲磺酰胺) 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 56.0h， 生成 [(4S)-5-oxo-4-tri(propan-2-yl)silyloxypentyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Catalytic asymmetric synthesis of protected α-hydroxy aldehydes and related 1,2-difunctional chiral building blocks. An enantioselective synthesis of (−)-exo- and (−)-endo-brevicomin

  摘要：

  Chiral allylic alcohols which were prepared by the addition of functionalized dialkylzincs to alpha,beta-unsaturated aldehydes in good to excellent enantioselectivity, were converted to protected alpha-hydroxy aldehydes and 1,2-amino alcohols without loss of enantiomeric purity. Syn- or anti-1,2-diols can be obtained stereoselectively by a second asymmetric addition to alpha-silyloxy aldehydes. Functionalized 1,2-diols prepared in this way were converted to enantiomerically pure (-)-exo- and (-)-endo-brevicomin (>99% ee). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00036-0

文献信息

• Catalytic asymmetric synthesis of protected α-hydroxy aldehydes and related 1,2-difunctional chiral building blocks. An enantioselective synthesis of (−)-exo- and (−)-endo-brevicomin
  作者：S. Vettel、C. Lutz、A. Diefenbach、G. Haderlein、S. Hammerschmidt、K. Kühling、M.-R. Mofid、T. Zimmermann、P. Knochel

  DOI：10.1016/s0957-4166(97)00036-0

  日期：1997.3

  Chiral allylic alcohols which were prepared by the addition of functionalized dialkylzincs to alpha,beta-unsaturated aldehydes in good to excellent enantioselectivity, were converted to protected alpha-hydroxy aldehydes and 1,2-amino alcohols without loss of enantiomeric purity. Syn- or anti-1,2-diols can be obtained stereoselectively by a second asymmetric addition to alpha-silyloxy aldehydes. Functionalized 1,2-diols prepared in this way were converted to enantiomerically pure (-)-exo- and (-)-endo-brevicomin (>99% ee). (C) 1997 Elsevier Science Ltd.