(2S,3S,4R)-1-(benzyloxy)-3,4-bis(tert-butyldimethylsilyloxy)-16-methylheptadecan-2-amine | 1388155-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,4R)-1-(benzyloxy)-3,4-bis(tert-butyldimethylsilyloxy)-16-methylheptadecan-2-amine
• 英文别名: (2S,3S,4R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-16-methyl-1-phenylmethoxyheptadecan-2-amine
• CAS: 1388155-20-1
• 化学式: C₃₇H₇₃NO₃Si₂
• 分子量: 636.163
• InChiKey: QNTHHKZSLMVMQU-XFQWPLCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.26
• 重原子数：
  43
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  53.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-1-(benzyloxy)-3,4-bis(tert-butyldimethylsilyloxy)-16-methylheptadecan-2-amine 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 palladium(II) hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.0h， 生成 (R)-N-((2S,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-1-hydroxy-16-methylheptadecan-2-yl)-2-(tert-butyldimethylsilyloxy)tetracosanamide
  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：

  (R)-2-(tert-butyldimethylsilyloxy)-14-methylpentadecanal 在 2,6-二甲基吡啶 、 盐酸 、 samarium diiodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 9.0h， 生成 (2S,3S,4R)-1-(benzyloxy)-3,4-bis(tert-butyldimethylsilyloxy)-16-methylheptadecan-2-amine
  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