Published as part of the Bürgenstock Special Section 2017 Future­ Stars in Organic Chemistry

Abstract

7-Substituted 4-methylcoumarin derivatives are widely employed as photoprotecting groups in chemistry and biology. We have recently shown that the 7-azetidinylated version of this photocage releases carboxylic acids in aqueous solution more efficiently than the traditionally used 7-diethylamino variant. Here we present a robust and scalable route to prepare the 7-azetidinylated alcohol, a useful precursor for the photoprotection of a variety of leaving groups, and its use in the preparation of model phosphate, sulfonate, and carbamate derivatives.

7-Substituted 4-methylcoumarin derivatives are widely employed as photoprotecting groups in chemistry and biology. We have recently shown that the 7-azetidinylated version of this photocage releases carboxylic acids in aqueous solution more efficiently than the traditionally used 7-diethylamino variant. Here we present a robust and scalable route to prepare the 7-azetidinylated alcohol, a useful precursor for the photoprotection of a variety of leaving groups, and its use in the preparation of model phosphate, sulfonate, and carbamate derivatives.

中文翻译：

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实用和可扩展合成的7-氮杂环丁烷-1-基-4-（羟甲基）香豆素：改进的光可去除基团。

作为Bürgenstock专栏2017年有机化学中的未来之星的一部分发布

抽象的

7-取代的4-甲基香豆素衍生物在化学和生物学中被广泛用作光保护基团。我们最近显示，这种光笼的7-氮杂环丁烷基化版本比传统使用的7-二乙氨基变体更有效地在水溶液中释放羧酸。在这里，我们提出了一种稳健且可扩展的途径来制备7-氮杂环丁烷基化的醇（一种对各种离去基团进行光保护的有用前体）及其在制备模型磷酸盐，磺酸盐和氨基甲酸酯衍生物中的用途。

7-取代的4-甲基香豆素衍生物在化学和生物学中被广泛用作光保护基团。我们最近显示，这种光笼的7-氮杂环丁烷基化版本比传统使用的7-二乙氨基变体更有效地在水溶液中释放羧酸。在这里，我们提出了一种稳健且可扩展的途径来制备7-氮杂环丁烷基化的醇（一种对各种离去基团进行光保护的有用前体）及其在制备模型磷酸盐，磺酸盐和氨基甲酸酯衍生物中的用途。