Synthesis of 2‘,3‘-Didehydro-2‘,3‘-dideoxynucleosides by Reaction of 5‘-Protected Nucleoside 2‘,3‘-Dimesylates with Telluride Dianion: A General Route from <i>Cis</i> Vicinal Diols to Olefins
作者:Derrick L. J. Clive、Philip L. Wickens、Paulo W. M. Sgarbi
DOI:10.1021/jo9610570
日期:1996.1.1
treatment with telluride dianion in the form of the sodium or lithium salt. The method is well-suited to the preparation of unsaturated nucleosides that can be converted into compounds that are believed to be useful in the treatment of AIDS. The deoxygenation is general for vicinal dimesylates that have, or may adopt, a synperiplanar conformation. With straight chain compounds the reaction is stereospecific
通过用钠或锂盐形式的碲化物二价阴离子处理,将5'-保护的核苷的2',3'-二甲磺酸酯转化为相应的2',3'-二氢-2',3'-二脱氧化合物。该方法非常适合于不饱和核苷的制备,该不饱和核苷可以转化为据信可用于治疗艾滋病的化合物。脱氧通常用于具有或可以采用间平面构象的邻近二甲基酯。对于直链化合物,反应是立体特异性的。在某些情况下,可以用硒化物二价阴离子进行类似但较慢的脱氧。