p-nitrophenyl 8-phenyloctanoate | 1337559-20-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: p-nitrophenyl 8-phenyloctanoate
• CAS: 1337559-20-2
• 化学式: C₂₀H₂₃NO₄
• 分子量: 341.407
• InChiKey: CPHNEFPLGPCKBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  25.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 8-phenyloctanoate 、 (1R)-1-[(2R,3R)-3-[[(2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]oxiran-2-yl]pentadecan-1-ol 在 sodium azide 、 水 、 氯化铵 、 1,3-丙二硫醇 、 三乙胺 、 4-二甲氨基吡啶 作用下， 以 甲乙醚 、 甲醇 、 四氢呋喃 为溶剂， 反应 88.0h， 以15 mg的产率得到1-deoxy-1-[(2'S,3'S,4'R)-2'-(N-(8''-phenyloctanoyl)amino)-3',4'-dihydroxyoctadecyl]-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose
  参考文献：
  名称：

  Total Synthesis of α-1C-Galactosylceramide, an Immunostimulatory C-Glycosphingolipid, and Confirmation of the Stereochemistry in the First-Generation Synthesis

  摘要：

  A nonisosteric alpha-C-glycoside analogue of KRN7000 (alpha-1C-GalCer, 1) was reported to induce a selective type of cytokine release in human invariant natural killer cells in vitro. We report here a very concise synthetic route to 1 and its analogue 1'. The key steps include olefin cross-metathesis, Sharpless asymmetric epoxidation, and epoxide opening by NaN3/NH4Cl. Inversion of configuration at the amide-bearing carbon in the phytosphingosine backbone constructed by epoxide opening in our previous synthesis of 1 was verified, indicating that remote group participation is not involved during the epoxide-opening reaction.

  DOI：

  10.1021/jo201450s