(R)-4-(4''-methoxybenzyloxy)-1-((2'R,3'R)-3'-pentadecyloxiran-2'-yl)but-2-yn-1-ol | 1337559-53-1

• 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: (R)-4-(4''-methoxybenzyloxy)-1-((2'R,3'R)-3'-pentadecyloxiran-2'-yl)but-2-yn-1-ol
• 英文别名: (1R)-4-[(4-methoxyphenyl)methoxy]-1-[(2R,3R)-3-pentadecyloxiran-2-yl]but-2-yn-1-ol
• CAS: 1337559-53-1
• 化学式: C₂₉H₄₆O₄
• 分子量: 458.682
• InChiKey: IUAWPDCCJAAYRD-MPFGFTFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  33
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-4-(4''-methoxybenzyloxy)-1-((2'R,3'R)-3'-pentadecyloxiran-2'-yl)but-2-yn-1-ol 在 sodium azide 、 水 、 氯化铵 作用下， 以 甲乙醚 为溶剂， 反应 48.0h， 以87%的产率得到(4R,5S,6S)-3-((4'-methoxybenzyloxy)methyl)-5,6-dihydro-6-pentadecyl-4H-pyrrolo[1,2-e][1,2,3]-triazole-4,5-diol
  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
• 作为产物：
  描述：

  (E)-1-(4'-methoxybenzyloxy)henicos-5-en-2-yn-4-ol 在 titanium(IV) isopropylate 、 过氧化氢异丙苯 、 D-(-)-酒石酸二异丙酯 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到(R)-4-(4''-methoxybenzyloxy)-1-((2'R,3'R)-3'-pentadecyloxiran-2'-yl)but-2-yn-1-ol
  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