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新产品编号:1134803

Chemical Name: O-(6-Deoxy-alpha-L-galactopyranosyl)-N-(2-tetradecylhexadecanoyl)-D-seryl-L-glutamic acid 1-methylamide
项目整合开发状态: Biological Testing
项目研究机构: Kanebo (Originator)
合成路线:Condensation of protected fucopyranose (I) with Z-serine methyl ester (II) in the presence of trimethylsilyl triflate afforded fucosylated serine derivative (III).Then,selective elimination of benzyloxycarbonyl group was performed by hydrogenolysis in the presence of Pd/C to give amine (IV).Subsequent coupling with acid (V) using EDC and HOBt as the condensing reagents provided amide (VI).Hydrolysis of ester group of (VI) by treatment with LiI in pyridine gave acid (VII),which was condensed with glutamic acid derivative (VIII) to yield (IX).Finally,debenzylation of (IX) by hydrogenolysis in the presence of Pd(OH)2 provided the target compound.
📌 参考资料/链接:
参考文献标题:A stereoselective alpha-fucosylation reaction using 1-hydroxy 2,3,4-tri-O-benzyl-L-fucose donor for the practical synthesis of selectin blocker
文献作者:Kiyoi,T.; Kondo,H.
参考来源:Bioorg Med Chem Lett 1998,8(20),2845