1-[(S,E)-4-hydroxyoctadec-2-en-5-ynyl]-3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-galactopyranose | 1337559-43-9

• 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-[(S,E)-4-hydroxyoctadec-2-en-5-ynyl]-3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-galactopyranose
• 英文别名: (E,4S)-1-[(2R,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]octadec-2-en-5-yn-4-ol
• CAS: 1337559-43-9
• 化学式: C₄₅H₆₀O₅
• 分子量: 680.968
• InChiKey: TZMPBCWWYSIGGH-MREGPSIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  50
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 (R,R)-(-)-2,6-bis[2-(hydroxyldiphenylmethyl)-1-pyrrolidinyl-methyl]-4-methylphenole 、 Dimethylzinc 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 314.75h， 生成 1-[(S,E)-4-hydroxyoctadec-2-en-5-ynyl]-3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-galactopyranose 、 1-[(R,E)-4-hydroxyoctadec-2-en-5-ynyl]-3,4,6-tri-O-benzyl-1,2-dideoxy-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

文献信息

• Total Synthesis of α-1<i>C</i>-Galactosylceramide, an Immunostimulatory <i>C</i>-Glycosphingolipid, and Confirmation of the Stereochemistry in the First-Generation Synthesis
  作者：Zheng Liu、Hoe-Sup Byun、Robert Bittman

  DOI：10.1021/jo201450s

  日期：2011.11.4

  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.