(4R,5S,6S)-6-[[(2R,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]-3-dodecyl-5,6-dihydro-4H-pyrrolo[1,2-c]triazole-4,5-diol | 1337559-49-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5S,6S)-6-[[(2R,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]-3-dodecyl-5,6-dihydro-4H-pyrrolo[1,2-c]triazole-4,5-diol
• CAS: 1337559-49-5
• 化学式: C₄₅H₆₁N₃O₆
• 分子量: 739.996
• InChiKey: LGDXCFRHUFKWDW-ARMINNDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  54
• 可旋转键数：
  23
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4R,5S,6S)-6-[[(2R,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]-3-dodecyl-5,6-dihydro-4H-pyrrolo[1,2-c]triazole-4,5-diol 、 乙酸酐 在 吡啶 作用下， 以91%的产率得到[(4R,5S,6S)-4-acetyloxy-6-[[(2R,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]-3-dodecyl-5,6-dihydro-4H-pyrrolo[1,2-c]triazol-5-yl] acetate
  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：

  在 sodium azide 、 水 、 氯化铵 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 48.0h， 以82%的产率得到(4R,5S,6S)-6-[[(2R,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]-3-dodecyl-5,6-dihydro-4H-pyrrolo[1,2-c]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