| 吉西他宾中间体的合成新工艺 |
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| 引用本文： | 周勇,孙爱丽,李伟,韩凌.吉西他宾中间体的合成新工艺[J].精细石油化工,2009,26(3). |
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| 作者姓名： | 周勇 孙爱丽 李伟 韩凌 |
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| 作者单位： | 1. 新乡学院化学与化工学院,河南,新乡,453000
2. 河南师范大学化学与环境科学学院,河南,新乡,453002 |
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| 基金项目： | 河南省教育厅自然科学研究资助计划项目 |
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| 摘 要： | 从D-甘露醇出发,经NaIO_4氧化、Reformasty反应、脱去异丙叉基保护基团、自身成环合成了吉西他宾关键中间体3,5-双-O-苯甲酰基-2-脱氧-2,2-二氟-1-氧代-D-呋喃核糖。对二氟五元核糖糖环结构中二氟的引入和3-位羟基手性的控制关键反应条件进行了优化。结果表明,将未活化的锌粉加入三烷基氯硅烷、未经重结晶的2,3-O-异丙亚基-D-甘油醛直接参与反应,反应温度45℃,顺反产物的选择性提高到1:13,关键中间体3R,3S-2,2-二氟-3-羟基-3-(2,2-二甲基-1,3-二氧戊环-4-基)戊酸乙酯的合成时间从4 d缩短到3～12 h,目标产物质量总收率76.4%。产物结构经IR与~1H NMR确证。
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| 关 键 词： | 吉西他宾 3 5-双-O-苯甲酰基-2-脱氧-2 2-二氟-1-氧代-D-呋喃核糖 D-甘露醇 合成 |
SYNTHESIS OF INTERMEDIATES FOR GEMCITABINE |
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| Zhou Yong,Sun Aili,Li Wei,Han Ling.SYNTHESIS OF INTERMEDIATES FOR GEMCITABINE[J].Speciality Petrochemicals,2009,26(3). |
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| Authors: | Zhou Yong Sun Aili Li Wei Han Ling |
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| Affiliation: | Zhou Yong~1,Sun Aili~1,Li Wei~2 and Han Ling~2 (1.College of Chemistry and Chemical Engineering,Xinxiang University,Xinxiang 453003,He'nan,China,2.College of Chemistry and Environmental Science,Henan Normal University,Xinxiang 453002,China) |
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| Abstract: | Starting from D-mannital,the key intermediate of gemcitabine,3,5-di-O-benzoyl-2-deoxy-2 and 2-difluoro-l-oxo-ribofuranose,was synthesized through sodium periodate oxidation,Reformasty reaction,separating the protective moieties of iso-propyl-benzyliden and cyclization.The introduction of difluoro in the saccharide ring of difluoro-pentahydric-ribose and the control of 3-hydroxyl chirality were optimized.Under the following optimized conditions,i.e.,directly adding inactive zinc powder into trialkyl-phosphin... |
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| Keywords: | gemcitabine 3 5-di-O-benzoyl-2-deoxy-2 2-difluoro-l-oxo-ribofuranose D-mannital synthesize |
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