[(3R,4S,9R,11R)-27-[4-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3S,4R,5R,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-3-methoxy-6-methyloxan-2-yl]oxyphenyl]-3-methoxy-4-methyl-9-[(2R,4R,6R,8R)-2,4,6,8-tetramethyloctacosanoyl]oxyheptacosan-11-yl] (2R,4R,6R,8R)-2,4,6,8-tetramethyloctacosanoate | 1425472-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3R,4S,9R,11R)-27-[4-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3S,4R,5R,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-3-methoxy-6-methyloxan-2-yl]oxyphenyl]-3-methoxy-4-methyl-9-[(2R,4R,6R,8R)-2,4,6,8-tetramethyloctacosanoyl]oxyheptacosan-11-yl] (2R,4R,6R,8R)-2,4,6,8-tetramethyloctacosanoate
• CAS: 1425472-02-1
• 化学式: C₁₂₁H₂₂₆O₁₈
• 分子量: 1969.11
• InChiKey: FZUGPAQVCVHHAQ-OHVQGHCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  42
• 重原子数：
  139
• 可旋转键数：
  93
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  215
• 氢给体数：
  3
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  [(3R,4S,9R,11R)-3-methoxy-27-[4-[(2S,3R,4R,5S,6S)-3-methoxy-6-methyl-4-[(2S,3R,4R,5S,6S)-6-methyl-3,5-bis(phenylmethoxy)-4-[(2S,3S,4R,5R,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-phenylmethoxyoxan-2-yl]oxyphenyl]-4-methyl-9-[(2R,4R,6R,8R)-2,4,6,8-tetramethyloctacosanoyl]oxyheptacos-26-yn-11-yl] (2R,4R,6R,8R)-2,4,6,8-tetramethyloctacosanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 20.0h， 以86%的产率得到[(3R,4S,9R,11R)-27-[4-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3S,4R,5R,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-3-methoxy-6-methyloxan-2-yl]oxyphenyl]-3-methoxy-4-methyl-9-[(2R,4R,6R,8R)-2,4,6,8-tetramethyloctacosanoyl]oxyheptacosan-11-yl] (2R,4R,6R,8R)-2,4,6,8-tetramethyloctacosanoate
  参考文献：
  名称：

  结核分枝杆菌的三糖基酚醛糖脂PGL-tb1的全合成

  摘要：

  复杂：结核分枝杆菌高毒力菌株外膜中糖脂PGL-tb1的合成首次通过高度融合的策略实现，该策略以Sonogashira偶联为特征，将酚三糖与苯硫酚结合在一起。高效的不对称铜催化不饱和硫酯和环状烯酮的1,4加成反应已用于引入甲基。

  DOI：

  10.1002/anie.201206221

文献信息

• Total Synthesis of the Triglycosyl Phenolic Glycolipid PGL-tb1 from<i>Mycobacterium tuberculosis</i>
  作者：Santiago Barroso、Riccardo Castelli、Marc P. Baggelaar、Danny Geerdink、Bjorn ter Horst、Eva Casas-Arce、Herman S. Overkleeft、Gijsbert A. van der Marel、Jeroen D. C. Codée、Adriaan J. Minnaard

  DOI：10.1002/anie.201206221

  日期：2012.11.19

  Complex: The synthesis of the glycolipid PGL‐tb1 present in the outer membrane of hypervirulent strains of Mycobacterium tuberculosis has been accomplished for the first time by using a highly convergent strategy featuring a Sonogashira coupling to unite a phenolic trisaccharide with the phthiocerol. Efficient asymmetric Cu‐catalyzed 1,4‐additions to unsaturated thioesters and cyclic enones have been

  复杂：结核分枝杆菌高毒力菌株外膜中糖脂PGL-tb1的合成首次通过高度融合的策略实现，该策略以Sonogashira偶联为特征，将酚三糖与苯硫酚结合在一起。高效的不对称铜催化不饱和硫酯和环状烯酮的1,4加成反应已用于引入甲基。