(S)-1-(((1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-3-acetoxy-7-carboxy-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-6-oxo-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-2-yl)oxy)-N,2,3-trimethylbutan-2-aminium chloride | 1370547-58-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (S)-1-(((1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-3-acetoxy-7-carboxy-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-6-oxo-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-2-yl)oxy)-N,2,3-trimethylbutan-2-aminium chloride
• CAS: 1370547-58-2
• 化学式: C₃₉H₆₃NO₇*ClH
• 分子量: 694.393
• InChiKey: OLNQTUGVRBAPHH-LVKKDACTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.13
• 重原子数：
  48.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  111.16
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  (1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-7-carbamoyl-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-6-oxo-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-3-yl acetate 在 亚硝酸特丁酯 、 20 wt.% Pd(OH)2 on activated carbon 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 20.0~35.0 ℃ 、275.8 kPa 条件下， 反应 1.0h， 生成 (S)-1-(((1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-3-acetoxy-7-carboxy-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-6-oxo-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-2-yl)oxy)-N,2,3-trimethylbutan-2-aminium chloride
  参考文献：
  名称：

  Synthesis of Antifungal Glucan Synthase Inhibitors from Enfumafungin

  摘要：

  An efficient, new, and scalable semisynthesis of glucan synthase inhibitors 1 and 2 from the fermentation product enfumafungin 3 is described. The highlights of the synthesis include a high-yielding ether bond-forming reaction between a bulky sulfamidate 17 and alcohol 4 and a remarkably chemoselective, improved palladium(II)-mediated Corey-Yu allylic oxidation at the highly congested C-12 position of the enfumafungin core. Multi-hundred gram quantities of the target drug candidates 1 and 2 were prepared, in 12 linear steps with 25% isolated yield and 13 linear steps with 22% isolated yield, respectively.

  DOI：

  10.1021/jo300046v