(3aR,4S,6R,7S,7aS)-6-(((2S,3R,4R)-4-amino-2-hydroxy-4-methylhex-5-yn-3-yl)oxy)-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol | 1191097-95-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4S,6R,7S,7aS)-6-(((2S,3R,4R)-4-amino-2-hydroxy-4-methylhex-5-yn-3-yl)oxy)-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 1191097-95-6
• 化学式: C₁₆H₂₇NO₆
• 分子量: 329.393
• InChiKey: VUGRUCBUTJKLPF-VXCYEKAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.27
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  103.4
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3aR,4S,6R,7S,7aS)-6-(((2S,3R,4R)-4-amino-2-hydroxy-4-methylhex-5-yn-3-yl)oxy)-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol 、 氯甲酸烯丙酯 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 0.52h， 以81%的产率得到allyl ((3R,4R,5S)-5-hydroxy-4-(((3aR,4S,6R,7S,7aS)-7-hydroxy-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)oxy)-3-methylhex-1-yn-3-yl)carbamate
  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：

  在 2,6-二叔丁基-4-甲基吡啶 、 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 以71%的产率得到(3aR,4S,6R,7S,7aS)-6-(((2S,3R,4R)-4-amino-2-hydroxy-4-methylhex-5-yn-3-yl)oxy)-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol
  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