NPC(Microbes), CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu Tawi, India 180001.
Org Biomol Chem. 2012 Dec 7;10(45):9090-8. doi: 10.1039/c2ob26324f. Epub 2012 Oct 22.
Azidotrimethylsilylation of carbohydrates (monosaccharides and disaccharides) has been achieved in high yields under Mitsunobu conditions. The azidation of carbohydrates is effected at 0 °C essentially only at the primary alcoholic position in mono, di- and triols in protected/unprotected glycosides, whereas the remaining secondary hydroxyl groups got silylated. Surprisingly, no azidation of the secondary hydroxyls was observed in all the carbohydrate substrates. Applications of the methodology for the synthesis of amino sugars, triazoles and azasugars are reported.
在 Mitsunobu 条件下，碳水化合物（单糖和二糖）的叠氮三甲基硅烷化反应可以高产率进行。在保护/非保护糖苷中单、二和三醇中，碳水化合物的叠氮化作用在 0°C 下主要在伯醇位置上进行，而其余的仲羟基被硅烷基化。令人惊讶的是，在所有的碳水化合物底物中都没有观察到仲羟基的叠氮化反应。报道了该方法在氨基糖、三唑和氮杂糖合成中的应用。
