Synthesis of Sialyl Lewis X Ganglioside Analogs Containing A Variable Length Spacer Between the Sugar and Lipophilic Moieties
作者:Keisuke Adachi、Yutaka Yamada、Hiroaki Wada、Akihiko Kameyama、Hideharu Ishida、Makoto Kiso
DOI:10.1080/07328309808002340
日期:1998.5.1
Lew is X ganglioside analogs containing 4-(2-tetradecylhexadecanoylamino)benzyl group in place of ceramide and a variety of lengths of ethylene glycol chains as the spacer, have been synthesized. Glycosidation of O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-glacto-2-nonulopyranosylonate)-(2→3)-O-(4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1→4)-O-[(2,3,4-tri-O-acet
摘要合成了5个唾液酸Lew是X神经节苷脂类似物,它们含有4-(2-十四烷基十六烷酰氨基)苄基代替神经酰胺,并以各种长度的乙二醇链为间隔基。O-(5-乙酰氨基甲基-4,7,8,9-四-O-乙酰基-3,5-二脱氧-D-甘油-α-D-乳酸-2-壬基吡喃葡萄糖醛酸酯)-(2→3)的糖基化-O-(4-O-乙酰基-2,6-二-O-苯甲酰基-β-D-吡喃半乳糖基)-(1→4)-O-[(2,3,4-三-O-乙酰基α-L (fucopyranosyl)-((1→3)]-2,4-di-O-benzoyl-α-D-glucopyranosyltrichloroacetimidate(13)与低聚乙二醇单苄基醚衍生物9、10、11和12,由相应的低聚乙二醇制得通过使用3-氟化硼醚化物进行4-硝基苄基化,还原并用2-十四烷基十六烷酸进行N-酰化,得到相应的糖脂衍生物14、15、16和17。