(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]pentadecan-1-ol | 1233218-86-4

• 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: (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]pentadecan-1-ol
• CAS: 1233218-86-4
• 化学式: C₅₃H₆₈O₇
• 分子量: 817.119
• InChiKey: UVCHLCTWMNVBQF-VSKYSXIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  60
• 可旋转键数：
  27
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  78.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  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]pentadecan-1-ol 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 [(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
  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：

  (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 在 titanium(IV) isopropylate 、 过氧化氢异丙苯 作用下， 以 二氯甲烷 为溶剂， 反应 48.75h， 以84%的产率得到(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]pentadecan-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.