1-deoxy-1-[(E)-4'-hydroxyoctadec-2'-en-5'-ynyl]-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose | 949570-32-5

• 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: 1-deoxy-1-[(E)-4'-hydroxyoctadec-2'-en-5'-ynyl]-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose
• CAS: 949570-32-5
• 化学式: C₅₂H₆₆O₆
• 分子量: 787.092
• InChiKey: LXLMOSPZDQFCQC-IIDKBMDWSA-N

物化性质

• 沸点：
  827.4±65.0 °C(predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  1-deoxy-1-[(E)-4'-hydroxyoctadec-2'-en-5'-ynyl]-2,3,4,6-tetra-O-benzyl-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 、
  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