[(2S,3R,4S,6S)-6-[(2S,3R,4S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-6-[[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-2-methyloxan-3-yl]oxy-3-[(2S,4S,5R,6S)-4,5-diacetyloxy-6-methyloxan-2-yl]oxy-2-methyloxan-4-yl] acetate | 476469-57-5

• 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: [(2S,3R,4S,6S)-6-[(2S,3R,4S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-6-[[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-2-methyloxan-3-yl]oxy-3-[(2S,4S,5R,6S)-4,5-diacetyloxy-6-methyloxan-2-yl]oxy-2-methyloxan-4-yl] acetate
• CAS: 476469-57-5
• 化学式: C₅₃H₈₄O₁₆Si
• 分子量: 1005.33
• InChiKey: WNHYXVKUUAEQEY-OKTMCJEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.99
• 重原子数：
  70
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  190
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S,6S)-6-[(2S,3R,4S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-6-[[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-2-methyloxan-3-yl]oxy-3-[(2S,4S,5R,6S)-4,5-diacetyloxy-6-methyloxan-2-yl]oxy-2-methyloxan-4-yl] acetate 在 吡啶 、 氢氟酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以63%的产率得到
  参考文献：
  名称：

  Stereoselective Synthesis of l-Oliose Trisaccharide via Iterative Alkynol Cycloisomerization and Acid-Catalyzed Glycosylation

  摘要：

  [GRAPHICS]The synthesis of an all-alpha L-Oliose diastereomer of digitoxin provides valuable insights into the generality and protective-group dependence of acid-catalyzed glycosylations of glycals to 2-deoxycarbohydrates.

  DOI：

  10.1021/ol026886o
• 作为产物：
  描述：

  3,4-bis-(tert-butyldimethylsilyl)-1,5-anhydro-2,6-dideoxy-L-lyxo-hex-1-enitol 在 六羰基钨 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 氢溴酸 、 二异丁基氢化铝 、 溶剂黄146 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 86.0h， 生成 [(2S,3R,4S,6S)-6-[(2S,3R,4S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-6-[[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-2-methyloxan-3-yl]oxy-3-[(2S,4S,5R,6S)-4,5-diacetyloxy-6-methyloxan-2-yl]oxy-2-methyloxan-4-yl] acetate
  参考文献：
  名称：

  Stereoselective Synthesis of l-Oliose Trisaccharide via Iterative Alkynol Cycloisomerization and Acid-Catalyzed Glycosylation

  摘要：

  [GRAPHICS]The synthesis of an all-alpha L-Oliose diastereomer of digitoxin provides valuable insights into the generality and protective-group dependence of acid-catalyzed glycosylations of glycals to 2-deoxycarbohydrates.

  DOI：

  10.1021/ol026886o