1-deoxy-1-[(4'R,2'E)-4'-hydroxy-2'-octadecenyl]-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose | 1337559-27-9

• 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-deoxy-1-[(4'R,2'E)-4'-hydroxy-2'-octadecenyl]-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose
• 英文别名: (E,4R)-1-[(2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]octadec-2-en-4-ol
• CAS: 1337559-27-9
• 化学式: C₅₂H₇₀O₆
• 分子量: 791.124
• InChiKey: HEMSGLLDLSEIFC-RLOMUYOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  58
• 可旋转键数：
  29
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-deoxy-1-[(4'R,2'E)-4'-hydroxy-2'-octadecenyl]-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose 在 titanium(IV) isopropylate 、 sodium azide 、 过氧化氢异丙苯 、 水 、 D-(-)-酒石酸二异丙酯 、 氯化铵 作用下， 以 甲乙醚 、 二氯甲烷 为溶剂， 反应 88.0h， 生成 1-deoxy-1-[(2'S,3'S,4'R)-2'-(N-(8''-phenyloctanoyl)amino)-3',4'-dihydroxyoctadecyl]-2,3,4,6-tetra-O-benzyl-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
• 作为产物：
  描述：

  (2R)-2-[(4-methoxyphenyl)methoxy]hexadecanal 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-deoxy-1-[(4'R,2'E)-4'-hydroxy-2'-octadecenyl]-2,3,4,6-tetra-O-benzyl-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.