(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 | 1233218-90-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• CAS: 1233218-90-0
• 化学式: C₅₃H₇₁NO₇
• 分子量: 834.149
• InChiKey: FEOLIKVXRJODMK-FSNWURJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  61
• 可旋转键数：
  28
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 (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
  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.