(3aR,4S,6R,7S,7aR)-6-(((2S,3R,4R)-4-(((allyloxy)carbonyl)amino)-2,4-dimethyl-3,4-dihydro-2H-pyran-3-yl)oxy)-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-yl acetate | 1191097-98-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3aR,4S,6R,7S,7aR)-6-(((2S,3R,4R)-4-(((allyloxy)carbonyl)amino)-2,4-dimethyl-3,4-dihydro-2H-pyran-3-yl)oxy)-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-yl acetate
• CAS: 1191097-98-9
• 化学式: C₂₂H₃₃NO₉
• 分子量: 455.505
• InChiKey: BYCSNHYRLOYNGR-BIKYLYQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  110.78
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6R,7R,7aS)-4-(4-methoxyphenoxy)-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol 、 (3aR,4S,6R,7S,7aR)-6-(((2S,3R,4R)-4-(((allyloxy)carbonyl)amino)-2,4-dimethyl-3,4-dihydro-2H-pyran-3-yl)oxy)-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-yl acetate 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.5h， 以90%的产率得到
  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：

  C₂₀H₃₁NO₈ 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到(3aR,4S,6R,7S,7aR)-6-(((2S,3R,4R)-4-(((allyloxy)carbonyl)amino)-2,4-dimethyl-3,4-dihydro-2H-pyran-3-yl)oxy)-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-yl acetate
  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