methyl (2R)-2-[tert-butyl(dimethyl)silyl]oxy-12-oxododecanoate | 1244958-82-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2R)-2-[tert-butyl(dimethyl)silyl]oxy-12-oxododecanoate
• CAS: 1244958-82-4
• 化学式: C₁₉H₃₈O₄Si
• 分子量: 358.594
• InChiKey: LSZVSQISCOSDME-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  24
• 可旋转键数：
  15
• 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：

  methyl (2R)-2-[tert-butyl(dimethyl)silyl]oxy-12-oxododecanoate 在 正丁基锂 、 samarium diiodide 、 palladium 10% on activated carbon 、 氢气 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 、 叔丁醇 为溶剂， 反应 21.0h， 生成 N-((2S,3S,4R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-16-methylheptadecan-2-yl)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  A flexible approach to construct three contiguous chiral centers of sphingolipids, and asymmetric synthesis of d-ribo-phytosphingosine and its derivatives

  摘要：

  An efficient approach to build the three contiguous stereogenic centers of sphingosine unit starting from cheap glutamic acid is described. The key step of this approach is the SmI2-mediated cross-coupling of chiral N-tert-butanesulfinyl imine 11 with sterically hindered aliphatic aldehyde 9 or 21 to construct hydroxymethyl beta-amino alcohol 10 or 22 in high diastereoselectivity (>99%, de). The utility of this flexible method has been demonstrated in the synthesis of D-ribo-phytosphingosine 1, its two derivatives 18 and 29. Moreover, a practicable synthetic route for synthesis of various sphingolipids, ceramides, alpha-galactosylceramides and their derivatives is also described. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.120
• 作为产物：
  描述：

  methyl (2R)-2-[tert-butyl(dimethyl)silyl]oxy-5-oxopentanoate 在 正丁基锂 、 草酰氯 、 palladium 10% on activated carbon 、 氢气 、 palladium(II) hydroxide 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 21.0h， 生成 methyl (2R)-2-[tert-butyl(dimethyl)silyl]oxy-12-oxododecanoate
  参考文献：
  名称：

  A flexible approach to construct three contiguous chiral centers of sphingolipids, and asymmetric synthesis of d-ribo-phytosphingosine and its derivatives

  摘要：

  An efficient approach to build the three contiguous stereogenic centers of sphingosine unit starting from cheap glutamic acid is described. The key step of this approach is the SmI2-mediated cross-coupling of chiral N-tert-butanesulfinyl imine 11 with sterically hindered aliphatic aldehyde 9 or 21 to construct hydroxymethyl beta-amino alcohol 10 or 22 in high diastereoselectivity (>99%, de). The utility of this flexible method has been demonstrated in the synthesis of D-ribo-phytosphingosine 1, its two derivatives 18 and 29. Moreover, a practicable synthetic route for synthesis of various sphingolipids, ceramides, alpha-galactosylceramides and their derivatives is also described. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.120

文献信息

• Asymmetric synthesis of ceramide sphingolipid based on (2S,3S,4S)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidine lactam
  作者：Wen-Feng Huang、Qian-Ru Li、Lu-Men Chao、Xin-Sheng Lei、Bang-Guo Wei

  DOI：10.1016/j.tetlet.2010.06.001

  日期：2010.8

  A facile approach to the versatile chiral building block 2 was developed based on glutamic acid, whereby a new method for asymmetric synthesis of sex pheromone 1 was explored from cheap glutamic acid.

  基于谷氨酸开发了一种通用的手性结构单元2的简便方法，从而从廉价的谷氨酸​​中探索了一种不对称合成性信息素1的新方法。
• A flexible approach to construct three contiguous chiral centers of sphingolipids, and asymmetric synthesis of d-ribo-phytosphingosine and its derivatives
  作者：Cholmen Xarnod (Lu-Men Chao)、Wei Huang、Rong-Guo Ren、Ru-Cheng Liu、Bang-Guo Wei

  DOI：10.1016/j.tet.2012.05.120

  日期：2012.8

  An efficient approach to build the three contiguous stereogenic centers of sphingosine unit starting from cheap glutamic acid is described. The key step of this approach is the SmI2-mediated cross-coupling of chiral N-tert-butanesulfinyl imine 11 with sterically hindered aliphatic aldehyde 9 or 21 to construct hydroxymethyl beta-amino alcohol 10 or 22 in high diastereoselectivity (>99%, de). The utility of this flexible method has been demonstrated in the synthesis of D-ribo-phytosphingosine 1, its two derivatives 18 and 29. Moreover, a practicable synthetic route for synthesis of various sphingolipids, ceramides, alpha-galactosylceramides and their derivatives is also described. (c) 2012 Elsevier Ltd. All rights reserved.