2-邻苯二甲酰亚胺-2-去氧-β-D-半乳吡喃糖乙硫苷供体制备工艺的优化
Optimization on preparation of ethyl 2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside donor
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收稿日期： 年卷（期）页码：2020,35(04):-355-358
期刊名称：华西药学杂志
Journal Name：WEST CHINA JOURNAL OF PHARMACEUTICAL SCIENCES
关键字：硫酸软骨素;寡糖合成;2-氨基-2-去氧-D-半乳糖盐酸盐;邻苯二甲酰亚胺基;叔丁基二甲基硅基;乙硫苷供体;合成;制备工艺优化
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中文摘要
目的优化2-邻苯二甲酰亚胺-2-去氧-β-D-半乳吡喃糖乙硫苷供体的制备工艺。方法以2-氨基-2-去氧-D-半乳糖盐酸盐为原料,采用氨基保护、苯亚甲基化和硅基化等7步化学反应,利用1HNMR、13CNMR及LC-MS(ESI)验证化合物的结构。结果以总收率为25.4%制备了化合物Ⅰ。结论所用方法比报道的反应步骤减少两步,提高了制备效率。
英文摘要
[1]Mikami T,Kitagawa H.Biosynthesis and function of chondroitin sulfate[J].Biochimica et Biophysica Acta(BBA)-General Subjects,2013,1830(10):4719-4733．
[2]Zhu Z,Dong X,Yan C,et al.Structural features and digestive behavior of fucosylated chondroitin sulfate from sea cucumbers Stichopus japonicus[J].J Agric Food Chem,2019,67(37):10534-10542．
[3]王文爽，许莹莹，石立冉，等．海洋来源硫酸软骨素降解酶的研究进展[J]．生命科学，2019,31(9):894-901．
[4]Martin MS,Van Sell S,Danter J.Glucosamine and chondroitin:An appropriate adjunct treatment of symptomatic osteoarthritis of the knee[J].Orthop Nurs,2012,31(3):160-166．
[5]李艳平，吴拥军，常佩亮，等．化学发光法快速测定硫酸软骨素注射液的含量[J]．华西药学杂志，2007,22(3):331-332．
[6]Kwok JC,Warren P,Fawcett JW.Chondroitin sulfate:A key molecule in the brain matrix[J].Int J Biochem Cell Biol,2012,44(4):582-586．
[7]Sotogaku N,Tully SE,Gama CI,et al.Activation of phospholipase C pathways by a synthetic chondroitin sulfate-Etetrasaccharide promotes neurite outgrowth of dopaminergic neurons[J].J Neurochem,2007,103(2):749-760．
[8]马敏，史雪莹，刘黎莎，等．硫酸软骨素药理学活性研究进展[J]．食品与药品，2017,19(6):450-455．
[9]周跃钢．硫酸软骨素的研究进展及其应用前景[J]．中国药学杂志，2016,51(21):1821-1825．
[10]Tully SE,Mabon R,Gama CI,et al.A chondroitin sulfate small molecule that stimulates neuronal growth[J].J Am Chem Soc,2004,126(25):7736-7737．
[11]Yang S,Liu Q,Zhang G,et al.An approach to synthesize chondroitin sulfate-E(CS-E) oligosaccharide precursors[J].J Org Chem,2018,83(11):5897-5908．
[12]Yu H,Yan X,Autran CA,et al.Enzymatic and chemoenzymatic syntheses of disialyl glycans and their necrotizing enterocolitis preventing effects[J].J Org Chem,2017,82(24):13152-13160．
[13]Hansson J,Garegg PJ,Oscarson S.Syntheses of anomerically phosphodiester-linked oligomers of the repeating units of the haemophilus influenzae types c and f capsular polysaccharides[J].J Org Chem,2001,66(19):6234-6243．
[14]Ellervik U,Magnusson G.Glycosylation with N-Trocprotected glycosyl donors[J].Carbohydr Res,1996,280(2):251-260．
[15]Zhang J,Otter A,Bundle DR.Synthesis and conformational studies of the tyvelose capped,Lewis x like tetrasaccharide epitope of Trichinella spiralis[J].Bioorg Med Chem,1996,4(11):1989-2001.
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