N-[(1R,2S,3R)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-heptadecyl]-acetamide | 787632-49-9

• 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: N-[(1R,2S,3R)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-heptadecyl]-acetamide
• CAS: 787632-49-9
• 化学式: C₃₅H₅₅NO₆
• 分子量: 585.825
• InChiKey: VQLAMSSRSRQUGP-VATRIRCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.62
• 重原子数：
  42.0
• 可旋转键数：
  24.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  86.25
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-[(1R,2S,3R)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-heptadecyl]-acetamide 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 以75%的产率得到N-acetyl L-arabino-(2R,3S,4R)-phytosphingosine
  参考文献：
  名称：

  Oxazine formation by MsCl/Et3N as a convenient tool for the stereochemical interconversion of the hydroxyl group in N-acetyl 1,3-aminoalcohols. Asymmetric synthesis of N-acetyl l-xylo- and l-arabino-phytosphingosines

  摘要：

  Use of MsCl/Et3N was proven to provide a convenient synthetic tool for the stereochemical intercoversion of the hydroxyl group in N-acetyl 1,3-aminoalcohols. Thus, under these conditions, the alcohols 4 and 6 smoothly converted to the oxazines 5 and 7, respectively, which were hydrolyzed to generate the corresponding inverted alcohols 6 and 4 in one pot. Further elaboration of 4 and 6 led to the efficient asymmetric synthesis of N-acetyl L-xylo- and L-arabino-phytosphingosines (11 and 15), respectively, via olefin cross metathesis reactions. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.08.030
• 作为产物：
  描述：

  1-十四烯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 8.0h， 生成 N-[(1R,2S,3R)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-heptadecyl]-acetamide
  参考文献：
  名称：

  Oxazine formation by MsCl/Et3N as a convenient tool for the stereochemical interconversion of the hydroxyl group in N-acetyl 1,3-aminoalcohols. Asymmetric synthesis of N-acetyl l-xylo- and l-arabino-phytosphingosines

  摘要：

  Use of MsCl/Et3N was proven to provide a convenient synthetic tool for the stereochemical intercoversion of the hydroxyl group in N-acetyl 1,3-aminoalcohols. Thus, under these conditions, the alcohols 4 and 6 smoothly converted to the oxazines 5 and 7, respectively, which were hydrolyzed to generate the corresponding inverted alcohols 6 and 4 in one pot. Further elaboration of 4 and 6 led to the efficient asymmetric synthesis of N-acetyl L-xylo- and L-arabino-phytosphingosines (11 and 15), respectively, via olefin cross metathesis reactions. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.08.030