Efficient syntheses of a series of glycosphingolipids with 1,2-trans-glycosidic linkages

被引:15
|
作者
Liu, Yunpeng [1 ]
Ding, Ning [1 ]
Xiao, Hualing [1 ]
Li, Yingxia [1 ]
机构
[1] Ocean Univ China, Sch Pharm, Minist Educ China, Key Lab Marine Drugs, Qingdao 266003, Peoples R China
关键词
glycosphingolipid with 1,2-trans-glycosidic linkage; Schmidt's; glycosyl trichloroacetimidate; Azido-sphingosine; glycosylation; conformation;
D O I
10.1080/07328300600859825
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of glycosphingolipids with 1,2-trans-glycosidic linkages were synthesized in the presence of neighboring group participation using trichloroacetimidates as glycosyl donors and an azido-sphingosine as the glycosyl acceptor. During the preparation of the target compounds, it was found that the alpha-L-arabinopyranosyl unit in target 7e and intermediates 7b - 7d existed in the C-1(4) conformation and that the b-L-fucopyranosyl unit in 10e adopted the C-4(1) conformation.
引用
收藏
页码:471 / 489
页数:19
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