A facile regio- and stereoselective synthesis of mannose octasaccharide of the N-glycan in human CD2 and mannose hexasaccharide antigenic factor 13b
作者:Yuliang Zhu、Langqiu Chen、Fanzuo Kong
DOI:10.1016/s0008-6215(01)00307-x
日期:2002.2
A highly concise and effective synthesis of the mannose octasaccharide of the N-linked glycan in the adhesion domain of human CD2 was achieved via TMSOTf-promoted selective 6-glycosylation of a trisaccharide 4,6-diol acceptor with a pentasaccharide donor, followed by deprotection. The pentasaccharide was constructed by selective 3,6-diglycosylation of 1,2-O-ethylidene-beta-D-mannopyranose with 2-O-acetyl-3
通过TMSOTf促进三糖4,6-二醇受体与五糖供体的选择性6-糖基化,然后脱保护,实现了在人CD2粘附域中N-连接聚糖的甘露糖八糖的高度简洁和有效的合成。 。通过用2-O-乙酰基-3,4,6-三-O-苯甲酰基-α-D-甘露吡喃糖基-对1,2-O-亚乙基-β-D-甘露吡喃糖进行选择性3,6-二糖基化来构建五糖。 (1-> 2)-3,4,6-三-O-苯甲酰基-α-D-甘露吡喃糖基三氯乙酰亚胺酸酯,而三糖是通过烯丙基4,6-O-亚苄基-α的选择性3-O-糖基化获得的-D-甘露吡喃糖苷与相同的二糖三氯乙酰亚胺酸酯,然后进行脱苄基作用。甘露糖六糖抗原因子13b是通过三糖供体2-O-乙酰-3,4,