[(2S,3S,4R)-2-acetamido-3,4-diacetyloxyhex-5-enyl] acetate | 1198410-14-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2S,3S,4R)-2-acetamido-3,4-diacetyloxyhex-5-enyl] acetate
• CAS: 1198410-14-8
• 化学式: C₁₄H₂₁NO₇
• 分子量: 315.323
• InChiKey: LRYUPQDXVFENIX-MJBXVCDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-十四烯 、 [(2S,3S,4R)-2-acetamido-3,4-diacetyloxyhex-5-enyl] acetate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以73%的产率得到(2S,3S,4R,5E)-2-acetamido-1,3,4-tri-O-acetyloctadec-5-ene-1,3,4-triol
  参考文献：
  名称：

  Efficient synthesis of d-xylo and d-ribo-phytosphingosines from methyl 2-amino-2-deoxy-β-d-hexopyranosides

  摘要：

  A general and flexible synthetic approach to biologically important 5,6-unsaturated C-18-phytosphingosines was developed via olefin cross-metathesis employing truncated C-6-phytosphingosines as the key intermediates. These were efficiently prepared in high yields by zinc-mediated reductive opening of methyl 2-amino-2-deoxy-beta-hexopyranosides.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.07.007
• 作为产物：
  描述：

  (2S,3S,4R)-2-acetamidohex-5-ene-1,3,4-triol 、 乙酸酐 在 吡啶 作用下， 反应 18.0h， 生成 [(2S,3S,4R)-2-acetamido-3,4-diacetyloxyhex-5-enyl] acetate
  参考文献：
  名称：

  Efficient synthesis of d-xylo and d-ribo-phytosphingosines from methyl 2-amino-2-deoxy-β-d-hexopyranosides

  摘要：

  A general and flexible synthetic approach to biologically important 5,6-unsaturated C-18-phytosphingosines was developed via olefin cross-metathesis employing truncated C-6-phytosphingosines as the key intermediates. These were efficiently prepared in high yields by zinc-mediated reductive opening of methyl 2-amino-2-deoxy-beta-hexopyranosides.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.07.007