(E,3R)-1-iodoheptadec-1-en-3-ol | 1233218-79-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E,3R)-1-iodoheptadec-1-en-3-ol
• CAS: 1233218-79-5
• 化学式: C₁₇H₃₃IO
• 分子量: 380.353
• InChiKey: NHUWAZVQEBUABY-INFVRCAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E,3R)-1-iodoheptadec-1-en-3-ol 、 (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)ethyne 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以88%的产率得到(E,5R)-1-[(2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]nonadec-3-en-1-yn-5-ol
  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：

  (R,E)-1-(((1-iodoheptadec-1-en-3-yl)oxy)methyl)-4-methoxybenzene 在 甲醇 、 碘 作用下， 反应 2.0h， 以75%的产率得到(E,3R)-1-iodoheptadec-1-en-3-ol
  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