文献类型：期刊文献

英文题名：SYNTHESIS OF NELARABINE WITH PURE beta-ANOMER THROUGH LATE-STAGE C-H NITRATION/NITRO-REDUCTION

作者：Xia, Ran[1];Sun, Li-Ping[1];Qu, Gui-Rong[2]

第一作者：夏然

通讯作者：Xia, R[1]

机构：[1]Xinxiang Univ, Sch Life Sci & Technol, Dept Chem & Chem Engn, Xinxiang 453003, Peoples R China;[2]Henan Normal Univ, Coll Chem & Chem Engn, Xinxiang 453007, Peoples R China

第一机构：新乡学院生命科学技术学院|新乡学院化学化工学院

通讯机构：[1]corresponding author), Xinxiang Univ, Sch Life Sci & Technol, Dept Chem & Chem Engn, Xinxiang 453003, Peoples R China.|[110713]新乡学院化学化工学院;[11071]新乡学院;[1107115]新乡学院生命科学技术学院;

年份：2015

卷号：91

期号：12

起止页码：2386-2393

外文期刊名：HETEROCYCLES

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000369356300012)，CCR-EXPANDED(收录号:WOS:000369356300012)】；

语种：英文

摘要：An efficient and pure p-anomer synthesis of the clinical drug nelarabine from the readily available vidarabine has been achieved for the first time. The C6 amino group of vidarabine was transformed to methoxy group by diazotization/chlorination followed by methoxylation using Na2CO3/MeOH system. The formation of C(2)-N bond was achieved via the highly selective C-H bond functionalization by reacting with 2,2,2-trifluoroacetic anhydride (TFAA) and tetrabutylammonium nitrate. The final product was obtained in total yield of 58.6% by 5 steps-synthesis from vidarabine after the reduction of nitro group to amino group. Moreover, the drug nelarabine could be obtained in 100 grams scale successfully and no chromatography was needed, which made this route more attractive for industrial application.