(4S,5S,6R)-6-tetradecyl-2-(trichloromethyl)-4-[2-[(2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethynyl]-5,6-dihydro-4H-1,3-oxazin-5-ol | 1233218-87-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5S,6R)-6-tetradecyl-2-(trichloromethyl)-4-[2-[(2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethynyl]-5,6-dihydro-4H-1,3-oxazin-5-ol
• CAS: 1233218-87-5
• 化学式: C₅₅H₆₈Cl₃NO₇
• 分子量: 961.506
• InChiKey: WGDQUHGIWJUVBZ-FSNWURJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  66
• 可旋转键数：
  26
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  88
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4S,5S,6R)-6-tetradecyl-2-(trichloromethyl)-4-[2-[(2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethynyl]-5,6-dihydro-4H-1,3-oxazin-5-ol 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成
  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：

  [(1R)-1-[(2R,3R)-3-[2-[(2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethynyl]oxiran-2-yl]pentadecyl] 2,2,2-trichloroethanimidate 在 氯化二乙基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 24.0h， 以333 mg的产率得到(4S,5S,6R)-6-tetradecyl-2-(trichloromethyl)-4-[2-[(2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethynyl]-5,6-dihydro-4H-1,3-oxazin-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

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.