Isostere-Based Design of 8-Azacoumarin-Type Photolabile Protecting Groups: A Hydrophilicity-Increasing Strategy for Coumarin-4-ylmethyls

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• 作者：Tetsuo Narumi ; Hikaru Takano ; Nami Ohashi ; Akinobu Suzuki ; Toshiaki Furuta ; Hirokazu Tamamura
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：February 21, 2014
• 年：2014
• 卷：16
• 期：4
• 页码：1184-1187
• 全文大小：258K
• ISSN：1523-7052

文摘

Described is the development of 8-azacoumarin-4-ylmethyl groups as aqueous photolabile protecting groups. A key feature of the strategy is the isosteric replacement of the C7鈥揅8 enol double bond of the Bhc derivative with an amide bond, resulting in conversion of the chromophore from coumarin to 8-azacoumarin. This strategy makes dramatically enhanced water solubility and facile photocleavage possible.