(1S,2S,3R,4R,1'R)-2-hydroxymethyl-3-(1'-hydroxypentadecyl)-7-oxabicyclo[2.2.1]hept-5-ene | 287381-75-3

• 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: (1S,2S,3R,4R,1'R)-2-hydroxymethyl-3-(1'-hydroxypentadecyl)-7-oxabicyclo[2.2.1]hept-5-ene
• CAS: 287381-75-3
• 化学式: C₂₂H₄₀O₃
• 分子量: 352.558
• InChiKey: LSVLQGLBWGYRER-MLBCHFTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  25.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4R,1'R)-2-hydroxymethyl-3-(1'-hydroxypentadecyl)-7-oxabicyclo[2.2.1]hept-5-ene 在 咪唑 、 potassium dioxotetrahydroxoosmate(VI) 、 甲基磺酰胺 、 AD-mix-β 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 xylene 、 叔丁醇 为溶剂， 反应 14.0h， 生成 (2R,3R,4R)-1-t-butyldiphenylsilyloxy-2-trichloroacetylamino-3,4-octadecanediol
  参考文献：
  名称：

  Enantioselective synthesis of lyxo -(2 R ,3 R ,4 R )-C 18 -phytosphingosine using double stereodifferentiation 1

  摘要：

  lyxo-C-18-Phytosphingosine can be synthesized by the cis-dihydroxylation of an (E)-allylic trichloroacetamide obtained by an Overman rearrangement. A double stereodifferentiation using AD-mix-beta and an enantiomerically enriched (S)-allylic trichloroacetamide allowed the first synthesis of lyxo-(2R,3R,4R)-C-18-phytosphingosine with high diastereoselectivity (de = 94%) and excellent enantioselectivity (ee = 93%). This sphingosine was fully characterized by the physical and spectral data of the corresponding tetraacetate. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00106-3
• 作为产物：
  描述：

  (1R,2S,6S,7S)-4,10-Dioxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-ol 、 tetradecylmagnesium bromide 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (1S,2S,3R,4R,1'R)-2-hydroxymethyl-3-(1'-hydroxypentadecyl)-7-oxabicyclo[2.2.1]hept-5-ene 、 (1S,2S,3R,4R,1'S)-2-hydroxymethyl-3-(1'-hydroxypentadecyl)-7-oxabicyclo[2.2.1]hept-5-ene
  参考文献：
  名称：

  Enantioselective synthesis of lyxo -(2 R ,3 R ,4 R )-C 18 -phytosphingosine using double stereodifferentiation 1

  摘要：

  lyxo-C-18-Phytosphingosine can be synthesized by the cis-dihydroxylation of an (E)-allylic trichloroacetamide obtained by an Overman rearrangement. A double stereodifferentiation using AD-mix-beta and an enantiomerically enriched (S)-allylic trichloroacetamide allowed the first synthesis of lyxo-(2R,3R,4R)-C-18-phytosphingosine with high diastereoselectivity (de = 94%) and excellent enantioselectivity (ee = 93%). This sphingosine was fully characterized by the physical and spectral data of the corresponding tetraacetate. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00106-3