N-((3S,4S,5R)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)nonadec-1-yn-3-yl)hexacosanamide | 1233218-92-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-((3S,4S,5R)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)nonadec-1-yn-3-yl)hexacosanamide
• CAS: 1233218-92-2
• 化学式: C₇₉H₁₂₁NO₈
• 分子量: 1212.83
• InChiKey: JLMYPNALHFGMFT-XRQAEKRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.41
• 重原子数：
  88.0
• 可旋转键数：
  53.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  115.71
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-((3S,4S,5R)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)nonadec-1-yn-3-yl)hexacosanamide 在 三氟化硼乙醚 、 乙硫醇 作用下， 反应 24.0h， 以95%的产率得到
  参考文献：
  名称：

  Synthesis of Immunostimulatory α-C-Galactosylceramide Glycolipids via Sonogashira Coupling, Asymmetric Epoxidation, and Trichloroacetimidate-Mediated Epoxide Opening

  摘要：

  Stereocontrolled syntheses of alpha-C-GalCer (2) and its alpha-C-acetylenic analogue 6 were accomplished in high efficiency by a convergent construction strategy from 1-hexadecene and D-galactose. The key transformations include Sonogashira coupling, Sharpless asymmetric epoxidation, and Et(2)AlCl-catalyzed cyclization of an epoxytrichloroacetimidate to generate protected dihydrooxazine 21.

  DOI：

  10.1021/ol1009976
• 作为产物：
  描述：

  hexacosanoyl chloride 、 (3S,4S,5R)-3-amino-1-[(2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]nonadec-1-yne-4,5-diol 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以208 mg的产率得到N-((3S,4S,5R)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)nonadec-1-yn-3-yl)hexacosanamide
  参考文献：
  名称：

  Synthesis of Immunostimulatory α-C-Galactosylceramide Glycolipids via Sonogashira Coupling, Asymmetric Epoxidation, and Trichloroacetimidate-Mediated Epoxide Opening

  摘要：

  Stereocontrolled syntheses of alpha-C-GalCer (2) and its alpha-C-acetylenic analogue 6 were accomplished in high efficiency by a convergent construction strategy from 1-hexadecene and D-galactose. The key transformations include Sonogashira coupling, Sharpless asymmetric epoxidation, and Et(2)AlCl-catalyzed cyclization of an epoxytrichloroacetimidate to generate protected dihydrooxazine 21.

  DOI：

  10.1021/ol1009976