3-[[(3aR,4R,6S,7S,7aR)-2,2,6-trimethyl-4-prop-2-enoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy-diphenylmethyl]-N,N-dimethylaniline | 1220688-59-4

• 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: 3-[[(3aR,4R,6S,7S,7aR)-2,2,6-trimethyl-4-prop-2-enoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy-diphenylmethyl]-N,N-dimethylaniline
• CAS: 1220688-59-4
• 化学式: C₃₃H₃₉NO₅
• 分子量: 529.676
• InChiKey: ZQWRAFAGCUECOU-LMQGFNJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[[(3aR,4R,6S,7S,7aR)-2,2,6-trimethyl-4-prop-2-enoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy-diphenylmethyl]-N,N-dimethylaniline 在 甲醇 作用下， 反应 0.5h， 以86%的产率得到allyl 2,3-O-isopropylidene-α-L-rhamnopyranoside
  参考文献：
  名称：

  促进光化学裂解苄基CO键。在光不稳定的羟基保护基设计中的应用。

  摘要：

  通过向传统的三苯甲基（Tr）保护基的芳环的间位引入二甲基氨基，已经开发了一种新的对光不稳定的羟基保护基。

  DOI：

  10.1039/b922021f
• 作为产物：
  描述：

  allyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 、 3-(dimethylamino)-α,α-diphenylbenzenemethanol 1-acetate 以 甲苯 为溶剂， 反应 21.0h， 以83%的产率得到3-[[(3aR,4R,6S,7S,7aR)-2,2,6-trimethyl-4-prop-2-enoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy-diphenylmethyl]-N,N-dimethylaniline
  参考文献：
  名称：

  促进光化学裂解苄基CO键。在光不稳定的羟基保护基设计中的应用。

  摘要：

  通过向传统的三苯甲基（Tr）保护基的芳环的间位引入二甲基氨基，已经开发了一种新的对光不稳定的羟基保护基。

  DOI：

  10.1039/b922021f

文献信息

• Facilitated photochemical cleavage of benzylic C–O bond. Application to photolabile hydroxyl-protecting group design
  作者：Pengfei Wang、Lei Zhou、Xin Zhang、Xing Liang

  DOI：10.1039/b922021f

  日期：——

  A new photolabile hydroxyl-protecting group has been developed by introducing a dimethylamino group to the meta position of an aromatic ring of the traditional trityl (Tr) protecting group.

  通过向传统的三苯甲基（Tr）保护基的芳环的间位引入二甲基氨基，已经开发了一种新的对光不稳定的羟基保护基。
• [EN] PHOTO-ACTIVATED PROTECTING GROUPS<br/>[FR] GROUPES PROTECTEURS PHOTO-ACTIVÉS
  申请人：UAB RESEARCH FOUNDATION

  公开号：WO2010042596A3

  公开（公告）日：2010-07-01
• 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.