2,2-Dimethyl-propionic acid (S)-5-(tert-butyl-dimethyl-silanyloxy)-6-oxo-hexyl ester | 189069-72-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-Dimethyl-propionic acid (S)-5-(tert-butyl-dimethyl-silanyloxy)-6-oxo-hexyl ester
• CAS: 189069-72-5
• 化学式: C₁₇H₃₄O₄Si
• 分子量: 330.54
• InChiKey: HTBGMXPURPTCMC-AWEZNQCLSA-N

物化性质

• 沸点：
  364.3±37.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Predicted)

反应信息

• 作为反应物：
  描述：

  diethylzinc 、 2,2-Dimethyl-propionic acid (S)-5-(tert-butyl-dimethyl-silanyloxy)-6-oxo-hexyl ester 在 titanium(IV) isopropylate 、 (1R)-反-N,N′-1,2-环己二基双(1,1,1-三氟甲磺酰胺) 作用下， 生成 2,2-Dimethyl-propionic acid (5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-octyl ester 、 2,2-Dimethyl-propionic acid (5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-octyl ester
  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：

  2,2-Dimethyl-propionic acid (S)-5-(tert-butyl-dimethyl-silanyloxy)-6,7-dihydroxy-octyl ester 在 sodium periodate 作用下， 以 四氢呋喃 为溶剂， 生成 2,2-Dimethyl-propionic acid (S)-5-(tert-butyl-dimethyl-silanyloxy)-6-oxo-hexyl ester
  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