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.
A new photochemical method of C-N bond formation has been developed. A properly substituted trityl alcohol can cleave the benzylic C-O bond and replace it with a C-N bond which is stable under the irradiation conditions. The C-N bond can then be photochemically cleaved with the same light source when the nitrogen is protonated.
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-protectinggroup has been developed by introducing a dimethylamino group to the meta position of an aromatic ring of the traditional trityl (Tr) protecting group.