8-氧-叔丁基二甲基硅烷基-4,5-氧-羰基-3-去氧-β-D-甘露-2-辛酮糖甲酸酯烯丙基苷的合成
Synthesis of methyl( allyl 8-O-tert-butyldimethylsilyl-4,5-O-carbonyl-3-deoxy-β-D-mano-2-octulopyranosid) onate
作者：王鑫;杨劲松;
Author：
收稿日期： 年卷（期）页码：2017,32(05):-449-451
期刊名称：华西药学杂志
Journal Name：WEST CHINA JOURNAL OF PHARMACEUTICAL SCIENCES
关键字：8-氧-叔丁基二甲基硅烷基-4,5-氧-羰基-3-去氧-β-D-甘露-2-辛酮糖甲酸酯烯丙基苷;D-阿拉伯糖;Kdo受体;Cornforth反应;Kdo寡糖;立体选择性;合成
Key words：
基金项目：国家自然科学基金资助项目(批准号:21572145)
中文摘要
目的研究8-氧-叔丁基二甲基硅烷基-4,5-氧-羰基-3-去氧-β-D-甘露-2-辛酮糖甲酸酯烯丙基苷的合成。方法以草酰乙酸和D-阿拉伯糖为原料,通过cornforth反应、乙酰化、甲酯化、烯醇化、脱乙酰基、硅基化、碳酸酯化等7步反应制备目标化合物。结果与结论与文献谱图进行对照,确证目标化合物的结构,7步反应的总收率为22%,化合物的立体选择性较高,方法操作简单、易于实施,为含(2→7)苷键结构的Kdo寡糖制备奠定了基础。
英文摘要
[1]Cipolla L,Gabrielli L,Shaikh N,etal.Kdo:Acritical monosaccharide for bacteria viability[J].Nat Prod Rep,2010,27(11):1618-1629.
[2]Lodowska J,Wolny D,Weglarz L.The sugar 3-deoxy-D-manno-oct-2-ulosonic acid(Kdo)as a characteristic component of bacterial endotoxin-a review of its biosynthesis,function,and placement in the lipopolysaccharide core[J].Can J Microbiol,2013,59(10):645-655.
[3]Heath EC,Ghalambor EA.2-Keto-3-deoxy-octonate,a constituent of cell wall li-opolysaccharide preparations obtained from Escherichia coli[J].Biochem Biophys Res Commun,1963,10(4):340-345.
[4]黄家声,杨劲松.Kdo乙硫苷供体的合成[J].合成化学,2016,24(5):442-444.
[5]Kosma P,Gass J.Artificial antigens synthesis of polyacrylamide copolymers containing 3-deoxy-d-manno-2-octulopyranosylonic acid(Kdo)residues[J].Carbohydr Res,1987,167(15):39-54.
[6]Paulsen H,Hayauchi Y,Unger FM.Synthese von disaccharidenaus 3-desoxy-D-manno-2-octulosonsaure(Kdo)und D-glucosamine[J].Liebigs Ann Chem,1984,1984(7):1270-1287.
[7]Auzanneau FI,Szilagyi DC,Szabo L.Chemistry of bacterial endotoxins.part 6,synthesis of allyl 5-O-(α-Dmannopyranosy1)-(3-deoxy-α-D-manno-oct-2-ulopyranosid)onic acid and of ally1-(α-D-mannopyranosyl)-(3-deoxy-α-D-manno-oct-2-ulopyranosid)onic acid 4-phosphate and their copolymers with acrylamide[J].J Chem Soc Perkin Trans,1991,1991(1),803-809.
[8]Pokorny B,Kosma P.Synthesis of chlamydia lipopolysaccharide haptensthrough the use ofα-specific 3-iodo-Kdo fluoride glycosyl donors[J].Chem Eur J,2015,21(1):305-313.
【关闭】
