| N-半胱氨酰基-1,3,4,6-四-O-乙酰基-β-D-氨基葡萄糖的合成研究 |
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| 引用本文： | 谢文林,陈伟东,唐子龙,李同金,汪林发,杨大成.N-半胱氨酰基-1,3,4,6-四-O-乙酰基-β-D-氨基葡萄糖的合成研究[J].精细化工中间体,2008,38(3). |
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| 作者姓名： | 谢文林 陈伟东 唐子龙 李同金 汪林发 杨大成 |
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| 作者单位： | 1. 湖南科技大学,化学化工学院,分子构效关系湖南省高校重点实验室,湖南,湘潭,411201
2. 西南大学,化学化工学院,重庆,400715 |
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| 基金项目： | 湖南省教育厅资助项目
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湖南科技大学校科研和教改项目 |
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| 摘 要： | 以2-氨基-β-D-葡萄糖盐酸盐为起始原料,与苯甲醛反应得到氨基保护的中间体苯甲醛缩-β-D-氨基葡萄糖(1),1以乙酸酐-吡啶乙酰化、盐酸-乙酸乙酯溶液脱去氨基保护基合成重要中间体2-氨基-1,3,4,6-四-O-乙酰基-β-D-葡萄糖盐酸盐(2)。2与保护氨基酸Boc-Cys(CH2-U)-OH在缩合剂DIC/HOBt/DIEA的作用下偶联,合成目标产物N-(N-叔丁氧羰基-S-5'-尿嘧啶甲基半胱氨酰基)-1,3,4,6-四-O-乙酰基-β-D-氨基葡萄糖(3)的合成3,总收率为40.0%。产物结构经1HNMR、MS、IR得以确证。
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| 关 键 词： | 氨基葡萄糖 保护氨基酸 糖基化 修饰 |
Synthesis of of N-Cysteinyi-1,3,4,6-tetra-O-acetyl-β-D-glucosamine |
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| XIE Wen-lin,CHEN Wei-dong,TANG Zi-long,LI Tong-jin,WANG Lin-fa,YANG Da-cheng.Synthesis of of N-Cysteinyi-1,3,4,6-tetra-O-acetyl-β-D-glucosamine[J].Fine Chemical Intermediates,2008,38(3). |
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| Authors: | XIE Wen-lin CHEN Wei-dong TANG Zi-long LI Tong-jin WANG Lin-fa YANG Da-cheng |
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| Abstract: | 2-Amino-1,3,4,6-tetra-O-acetyl-β-D-glucosamine hydrochloride was synthesized with 2-amino-β-D- glucosamine hydrochloride as starting materials by using benzaldehyde as protective reagent of amino group,following acetylation of the hydroxy groups with acetyl anhydride and the removal of protection unit of amino group by HCl-EtOAc. Then glycosylated amino acids was synthesized through condensation of 2-amino-1,3,4,6-tetra-O-acetyl-β-D-glucosamine hydro -chloride with protected amino acid Boc-Cys(CH2-U)-OH in the presence of DIC/HOBt/DIEA in the overall yield of 40.0%。The structures of synthetic compounds were confirmed by IR ,MS and 1H NMR spectra. |
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| Keywords: | methallyloxyphenol benzofuranol cyclization optimization |
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