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1. 中国科学院上海药物研究所
2. 中国科学院上海药物研究所,上海,200031
Published:01 December 1993
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[1]章辛,杨正修,徐平,丁瑞勤.[15—~(14)C]双氢青蒿内酯的合成[J].核技术,1993(12):759-761.
Zhang Xin Yang Zhengxiu Xu Ping Ding Ruiqin. Synthesis of (15-14C) dihydroartenisilacton[J]. Nuclear techniques, 1993, (12): 759-761.
4-羰基-4-去甲四氢青蒿酸甲酯(3)与
14
CH
3
MgI起格氏反应得[
14
C]4-羟基四氢青蒿酸甲酯(4α)
4α经脱水和水解反应得[
14
C]二氢青蒿酸(5α)和它的异构物(6α)的混合物
用四氧化锇和N-甲基吗琳N-氧化物氧化即得[15-
14
C]双氢青蒿内酯(2α)和另一产物[15-
14
C]3
4-二羟基四氢青蒿酸(7α);还同时合成了相应的
13
C和氘标记化合物(2b
c)和(7b
c)。
Grignard addition of 14CH3MgI to methyl ester of 4-keto-4-nortetrahy-droartemisinic acid (3) gave (15-14C) 4-hydroxytetrahydroartemisinic ester (4 α). 4α was dehydrated with P-toluenesulfonic acid in benzene followed by alkaline hydrolysis to obtain a mixture of dihydroartemisinic acid (5 α) and its isomer (6α). The mixture was oxidized with OsO4 and N-methylmorpholine-N-oxide to give (15-14C) dihydroartemisilacton (2α) and (15-14C) 3
4-dihydroxyartemisinic acid (7α). In addition the corresponding 13C and 2H labelled compounds were also prepared.
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