N-((3S,4S,5R)-4-(((3aR,4S,6R,7S,7aR)-7-((tert-butyldimethylsilyl)oxy)-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)oxy)-5-hydroxy-3-methyl-1-(trimethylsilyl)hex-1-yn-3-yl)acetamide | 1191098-07-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-((3S,4S,5R)-4-(((3aR,4S,6R,7S,7aR)-7-((tert-butyldimethylsilyl)oxy)-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)oxy)-5-hydroxy-3-methyl-1-(trimethylsilyl)hex-1-yn-3-yl)acetamide
• CAS: 1191098-07-3
• 化学式: C₂₇H₅₁NO₇Si₂
• 分子量: 557.875
• InChiKey: NKGMOJFPTJPQSF-GICICZIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  95.48
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-((3S,4S,5R)-4-(((3aR,4S,6R,7S,7aR)-7-((tert-butyldimethylsilyl)oxy)-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)oxy)-5-hydroxy-3-methyl-1-(trimethylsilyl)hex-1-yn-3-yl)acetamide 在 三乙烯二胺 、 六羰基钨 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到N-((2R,3S,4S)-3-(((3aR,4S,6R,7S,7aS)-7-hydroxy-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)oxy)-2,4-dimethyl-3,4-dihydro-2H-pyran-4-yl)acetamide
  参考文献：
  名称：

  Brønsted Acid-Promoted Glycosylations of Disaccharide Glycal Substructures of the Saccharomicins

  摘要：

  An acid-promoted glycosylation and alkynol cycloisomerization sequence provided direct access to the 2-deoxytrisaccharide corresponding to the fucose-saccharosamine-digitoxose substructure of saccharomicin B. In the course of this work, the absolute stereochemistry of the repeating fucose-saccharosamine disaccharide of saccharomicins was also confirmed.

  DOI：

  10.1021/ol901923x
• 作为产物：
  描述：

  、 乙酸酐 以 四氢呋喃 为溶剂， 反应 6.0h， 以82%的产率得到N-((3S,4S,5R)-4-(((3aR,4S,6R,7S,7aR)-7-((tert-butyldimethylsilyl)oxy)-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)oxy)-5-hydroxy-3-methyl-1-(trimethylsilyl)hex-1-yn-3-yl)acetamide
  参考文献：
  名称：

  Brønsted Acid-Promoted Glycosylations of Disaccharide Glycal Substructures of the Saccharomicins

  摘要：

  An acid-promoted glycosylation and alkynol cycloisomerization sequence provided direct access to the 2-deoxytrisaccharide corresponding to the fucose-saccharosamine-digitoxose substructure of saccharomicin B. In the course of this work, the absolute stereochemistry of the repeating fucose-saccharosamine disaccharide of saccharomicins was also confirmed.

  DOI：

  10.1021/ol901923x