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。
2-Amino-1,3,4,6-tetra-O-acetyl-β-D-glucosamine hydrochloride was synthesized with 2-amino-43-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%o The structures of synthetic compounds were confirmed by IR , MS and ^1H NMR spectra.
出处
《精细化工中间体》
CAS
2008年第3期36-38,共3页
Fine Chemical Intermediates
基金
湖南省教育厅资助科研项目(07B021)
湖南科技大学博士启动基金(E50632)资助
关键词
氨基葡萄糖
保护氨基酸
糖基化
修饰
methallyloxyphenol
benzofuranol
cyclization
optimization
