[(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5S,6R)-5-acetyloxy-6-methyl-2-[(4S)-non-1-en-4-yl]oxy-4-phenylmethoxyoxan-3-yl]oxy-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-3-yl] 2-chloroacetate | 1130996-54-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5S,6R)-5-acetyloxy-6-methyl-2-[(4S)-non-1-en-4-yl]oxy-4-phenylmethoxyoxan-3-yl]oxy-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-3-yl] 2-chloroacetate
• CAS: 1130996-54-1
• 化学式: C₃₈H₆₁ClO₁₂Si
• 分子量: 773.434
• InChiKey: ZVDXBMYRMQCZSG-JMESLZLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  52
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5S,6R)-5-acetyloxy-6-methyl-2-[(4S)-non-1-en-4-yl]oxy-4-phenylmethoxyoxan-3-yl]oxy-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-3-yl] 2-chloroacetate 、 4-oxo-8-nonenoic acid 在 4-二甲氨基吡啶 、 4-(dimethylamino)pyridine hydrochloride 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到[(2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5S,6R)-5-acetyloxy-6-methyl-2-[(4S)-non-1-en-4-yl]oxy-4-phenylmethoxyoxan-3-yl]oxy-4-[tert-butyl(dimethyl)silyl]oxy-5-(2-chloroacetyl)oxy-3-hydroxyoxan-2-yl]methyl 4-oxonon-8-enoate
  参考文献：
  名称：

  Total Synthesis of Ipomoeassin F

  摘要：

  The first total synthesis of ipomoeassin F was carried out using a convergent approach that relied upon the use of Schmidt glycosidation technology for the coupling of two suitably protected monosaccharide fragments. After two steps, ring-closing metathesis was used to form the macrocyclic ring, and seven more steps then furnished ipomoeassin F. In vitro inhibitory activity against a four-panel cell line showed low nanomolar inhibitory activity.

  DOI：

  10.1021/ol900086b
• 作为产物：
  描述：

  [(4aR,6S,7R,8S,8aR)-6-[(2R,3R,4S,5S,6R)-5-acetyloxy-6-methyl-2-[(4S)-non-1-en-4-yl]oxy-4-phenylmethoxyoxan-3-yl]oxy-8-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] 2-chloroacetate 在 甲醇 、 camphor-10-sulfonic acid 作用下， 反应 23.5h， 以43%的产率得到[(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5S,6R)-5-acetyloxy-6-methyl-2-[(4S)-non-1-en-4-yl]oxy-4-phenylmethoxyoxan-3-yl]oxy-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-3-yl] 2-chloroacetate
  参考文献：
  名称：

  Total Synthesis of Ipomoeassin F

  摘要：

  The first total synthesis of ipomoeassin F was carried out using a convergent approach that relied upon the use of Schmidt glycosidation technology for the coupling of two suitably protected monosaccharide fragments. After two steps, ring-closing metathesis was used to form the macrocyclic ring, and seven more steps then furnished ipomoeassin F. In vitro inhibitory activity against a four-panel cell line showed low nanomolar inhibitory activity.

  DOI：

  10.1021/ol900086b