4-oxo-4-[[(2R,3R,4S,5S,6S)-3,4,5-tris(3-carboxypropanoyloxy)-6-[3-[[3-(dimethylamino)phenyl]-diphenylmethoxy]propoxy]oxan-2-yl]methoxy]butanoic acid | 1310450-22-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 4-oxo-4-[[(2R,3R,4S,5S,6S)-3,4,5-tris(3-carboxypropanoyloxy)-6-[3-[[3-(dimethylamino)phenyl]-diphenylmethoxy]propoxy]oxan-2-yl]methoxy]butanoic acid
• CAS: 1310450-22-6
• 化学式: C₄₆H₅₃NO₁₉
• 分子量: 923.922
• InChiKey: OSBVHZLYIHBMTQ-DLRLXMORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  66
• 可旋转键数：
  31
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  285
• 氢给体数：
  4
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  4-oxo-4-[[(2R,3R,4S,5S,6S)-3,4,5-tris(3-carboxypropanoyloxy)-6-[3-[[3-(dimethylamino)phenyl]-diphenylmethoxy]propoxy]oxan-2-yl]methoxy]butanoic acid 在 sodium carbonate 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.5h， 以37%的产率得到(2S,3S,4S,5S,6R)-2-[3-[[3-(dimethylamino)phenyl]-diphenylmethoxy]propoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  Development of Trityl-Based Photolabile Hydroxyl Protecting Groups

  摘要：

  A series of trityl-based photolabile hydroxyl protecting groups have been examined. These PPGs evolve from the traditional acid-labile trityl protecting group with proper electron-donating substituents. Structure-reactivity relationships have been explored. A m-dimethylamino group is crucial to achieve high photochemical deprotection efficiency. The o-hydroxyl group in 8 greatly improves the yield of the photochemical deprotection reaction, compared with the corresponding o-methoxyl-substituted counterpart 7. However, comparison between the photoreactions of 9 and 11 does not show similar structural relevance. The PPG in ether I (i.e., DMATr group) is structurally simple and easy to prepare and install. Its deprotection can be successfully carried out with irradiation of sunlight without requirement of photochemical devices.

  DOI：

  10.1021/jo200692c
• 作为产物：
  描述：

  丁二酸酐 、 (2S,3S,4S,5S,6R)-2-[3-[[3-(dimethylamino)phenyl]-diphenylmethoxy]propoxy]-6-(hydroxymethyl)oxane-3,4,5-triol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 4-oxo-4-[[(2R,3R,4S,5S,6S)-3,4,5-tris(3-carboxypropanoyloxy)-6-[3-[[3-(dimethylamino)phenyl]-diphenylmethoxy]propoxy]oxan-2-yl]methoxy]butanoic acid
  参考文献：
  名称：

  Development of Trityl-Based Photolabile Hydroxyl Protecting Groups

  摘要：

  A series of trityl-based photolabile hydroxyl protecting groups have been examined. These PPGs evolve from the traditional acid-labile trityl protecting group with proper electron-donating substituents. Structure-reactivity relationships have been explored. A m-dimethylamino group is crucial to achieve high photochemical deprotection efficiency. The o-hydroxyl group in 8 greatly improves the yield of the photochemical deprotection reaction, compared with the corresponding o-methoxyl-substituted counterpart 7. However, comparison between the photoreactions of 9 and 11 does not show similar structural relevance. The PPG in ether I (i.e., DMATr group) is structurally simple and easy to prepare and install. Its deprotection can be successfully carried out with irradiation of sunlight without requirement of photochemical devices.

  DOI：

  10.1021/jo200692c

文献信息

• Development of Trityl-Based Photolabile Hydroxyl Protecting Groups
  作者：Lei Zhou、Haishen Yang、Pengfei Wang

  DOI：10.1021/jo200692c

  日期：2011.8.5

  A series of trityl-based photolabile hydroxyl protecting groups have been examined. These PPGs evolve from the traditional acid-labile trityl protecting group with proper electron-donating substituents. Structure-reactivity relationships have been explored. A m-dimethylamino group is crucial to achieve high photochemical deprotection efficiency. The o-hydroxyl group in 8 greatly improves the yield of the photochemical deprotection reaction, compared with the corresponding o-methoxyl-substituted counterpart 7. However, comparison between the photoreactions of 9 and 11 does not show similar structural relevance. The PPG in ether I (i.e., DMATr group) is structurally simple and easy to prepare and install. Its deprotection can be successfully carried out with irradiation of sunlight without requirement of photochemical devices.