A new C(1)-auxiliary for anomeric stereocontrol in the synthesis of α-sialyl glycosides

被引:48
作者
Haberman, JM [1 ]
Gin, DY [1 ]
机构
[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA
关键词
D O I
10.1021/ol015854i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The installation of the novel N,N-dimethylglycolamide ester auxiliary onto the C(1)-position of protected neuraminic acid donors allows for the exploitation of C(1)-neighboring group participation to generate sialoside conjugates with good to excellent or-selectivity under a variety of sialylation protocols, including those that would otherwise lead to nonselective or beta -selective sialoside products.
引用
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页码:1665 / 1668
页数:4
相关论文
共 33 条
[1]   GLYCOSYLATION WITH SIALIC-ACID AT HO-3 OF 3 DIFFERENT O-PROTECTED D-GALACTOSIDES IN ACETONITRILE DICHLOROMETHANE AT LOW-TEMPERATURE [J].
BIRBERG, W ;
LONN, H .
TETRAHEDRON LETTERS, 1991, 32 (50) :7457-7458
[2]   Recent advances in O-sialylation [J].
Boons, GJ ;
Demchenko, AV .
CHEMICAL REVIEWS, 2000, 100 (12) :4539-+
[3]   8-O-sialylation of neuraminic acid [J].
Castro-Palomino, JC ;
Tsvetkov, YE ;
Schmidt, RR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) :5434-5440
[4]   STEREOSELECTIVE TOTAL SYNTHESES OF THE NATURALLY-OCCURRING ENANTIOMERS OF N-ACETYLNEURAMINIC ACID AND 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID - A NEW AND STEREOSPECIFIC APPROACH TO SIALO AND 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID CONJUGATES [J].
DANISHEFSKY, SJ ;
DENINNO, MP ;
CHEN, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) :3929-3940
[5]  
DENINNO MP, 1991, SYNTHESIS-STUTTGART, P583
[6]   Glycobiology: Toward understanding the function of sugars [J].
Dwek, RA .
CHEMICAL REVIEWS, 1996, 96 (02) :683-720
[7]   HIGHLY STEREOSELECTIVE ALPHA-SIALYLATION - SYNTHESIS OF GM(3)-SACCHARIDE AND A BIS-SIALIC ACID UNIT [J].
ERCEGOVIC, T ;
MAGNUSSON, G .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) :3378-3384
[8]   Synthesis of a bis(sialic acid) 8,9-lactam [J].
Ercegovic, T ;
Magnusson, G .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) :179-184
[9]   Recent advances in the chemoenzymatic synthesis of carbohydrates and carbohydrate mimetics [J].
Gijsen, HJM ;
Qiao, L ;
Fitz, W ;
Wong, CH .
CHEMICAL REVIEWS, 1996, 96 (01) :443-473
[10]   SYNTHETIC STUDIES ON SIALOGLYCOCONJUGATES .19. A FACILE, LARGE-SCALE PREPARATION OF THE METHYL 2-THIOGLYCOSIDE OF N-ACETYLNEURAMINIC ACID, AND ITS USEFULNESS FOR THE ALPHA-STEREOSELECTIVE SYNTHESIS OF SIALOGLYCOSIDES [J].
HASEGAWA, A ;
OHKI, H ;
NAGAHAMA, T ;
ISHIDA, H ;
KISO, M .
CARBOHYDRATE RESEARCH, 1991, 212 :277-281