(2R)-2-[(4-methoxyphenyl)methoxy]hexadecan-1-ol | 1233218-76-2

• 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: (2R)-2-[(4-methoxyphenyl)methoxy]hexadecan-1-ol
• CAS: 1233218-76-2
• 化学式: C₂₄H₄₂O₃
• 分子量: 378.596
• InChiKey: NZWWPNHPGWVHFC-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  27
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(4-methoxyphenyl)methoxy]hexadecan-1-ol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 水 、 碳酸氢钠 、 sodium bromide 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 1.17h， 以62%的产率得到(2R)-2-[(4-methoxyphenyl)methoxy]hexadecanal
  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)-1,2-十六烷二醇 、 4-甲氧基苯甲醛二甲缩醛 在 对甲苯磺酸 、 二异丁基氢化铝 作用下， 以 苯 、 正己烷 、 二氯甲烷 为溶剂， 以85%的产率得到(2R)-2-[(4-methoxyphenyl)methoxy]hexadecan-1-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

文献信息

• Synthesis of Immunostimulatory α-<i>C</i>-Galactosylceramide Glycolipids via Sonogashira Coupling, Asymmetric Epoxidation, and Trichloroacetimidate-Mediated Epoxide Opening
  作者：Zheng Liu、Hoe-Sup Byun、Robert Bittman

  DOI：10.1021/ol1009976

  日期：2010.7.2

  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.