SYNTHESIS OF SIALYL-TN ANTIGEN - REGIOSELECTIVE SIALYLATION OF A GALACTOSAMINE THREONINE CONJUGATE UNBLOCKED IN THE CARBOHYDRATE PORTION

被引:36
|
作者
LIEBE, B [1 ]
KUNZ, H [1 ]
机构
[1] UNIV MAINZ,INST ORGAN CHEM,D-55099 MAINZ,GERMANY
关键词
D O I
10.1016/S0040-4039(00)78495-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Regioselective and stereocontrolled formation of the sialyl-Tn antigen conjugate 6 was achieved by reacting the NeuNAc-2-xanthate 2 with the GalNAc threonine acceptor 5 bearing three hydroxy groups. Complete deprotection afforded the sialyl-Tn antigen structure 11.
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页码:8777 / 8778
页数:2
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