(1R)-1-[(2R,3R)-3-[[(2S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]oxiran-2-yl]pentadec-2-yn-1-ol | 1337559-46-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-1-[(2R,3R)-3-[[(2S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]oxiran-2-yl]pentadec-2-yn-1-ol
• CAS: 1337559-46-2
• 化学式: C₄₅H₆₀O₆
• 分子量: 696.968
• InChiKey: RJEFCFNBANRWSL-CUVSVMCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  51
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-[(E)-4-hydroxyoctadec-2-en-5-ynyl]-3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-galactopyranose 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， 生成 、 (1R)-1-[(2R,3R)-3-[[(2S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]oxiran-2-yl]pentadec-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