A novel sulfonamidoglycosylation of glycals

被引:51
作者
Colinas, PA [1 ]
Bravo, RD [1 ]
机构
[1] Natl Univ La Plata, Fac Ciencias Exactas, Dept Quim, LADECOR, RA-1900 La Plata, Argentina
关键词
D O I
10.1021/ol035838g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The sulfonamidoglycosylation of benzylated glycals using a catalytic amount of triphenylphosphine hydrobromide proceeded in a highly stereoselective fashion to give the beta anomers with good to high yields, This process was demonstrated with D-galactal and D-glucal. Two of the new N-2-(deoxyglycosyl)sulfonamides were tested as inhibitors of tumor cell growth in vitro and showed anti proliferative properties in the micromolar range.
引用
收藏
页码:4509 / 4511
页数:3
相关论文
共 17 条
[1]   A novel direct route to 2-deoxy-2-fluoro-aldoses and their corresponding derivatives [J].
Albert, M ;
Dax, K ;
Ortner, J .
TETRAHEDRON, 1998, 54 (19) :4839-4848
[2]   DIRECT PREPARATION OF 2-DEOXY-D-GLUCOPYRANOSIDES FROM GLUCALS WITHOUT FERRIER REARRANGEMENT [J].
BOLITT, V ;
MIOSKOWSKI, C ;
LEE, SG ;
FALCK, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) :5812-5813
[3]  
BRAVO MG, COMMUNICATION
[4]   APPLICATION OF THE GLYCAL ASSEMBLY METHOD TO THE CONCISE SYNTHESIS OF NEOGLYCOCONJUGATES OF LE(Y) AND LE(B) BLOOD-GROUP DETERMINANTS AND OF H-TYPE-I AND H-TYPE-II OLIGOSACCHARIDES [J].
DANISHEFSKY, SJ ;
BEHAR, V ;
RANDOLPH, JT ;
LLOYD, KO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) :5701-5711
[5]   AZAGLYCOSYLATION OF COMPLEX STANNYL ALKOXIDES WITH GLYCAL-DERIVED IODO SULFONAMIDES - A STRAIGHTFORWARD SYNTHESIS OF SIALYL-LEWIS-X ANTIGEN AND OTHER OLIGOSACCHARIDE DOMAINS [J].
DANISHEFSKY, SJ ;
KOSEKI, K ;
GRIFFITH, DA ;
GERVAY, J ;
PETERSON, JM ;
MCDONALD, FE ;
ORIYAMA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8331-8333
[6]   Cyclooxygenase inhibitors - current status and future prospects [J].
Dannhardt, G ;
Kiefer, W .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2001, 36 (02) :109-126
[7]  
Ferrier RJ, 2001, TOP CURR CHEM, V215, P153
[8]   SULFONAMIDOGLYCOSYLATION OF GLYCALS - A ROUTE TO OLIGOSACCHARIDES WITH 2-AMINOHEXOSE SUBUNITS [J].
GRIFFITH, DA ;
DANISHEFSKY, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (15) :5811-5819
[9]  
KIRBY AJ, 1983, ANOMERIC EFFECT RELA, pCHA
[10]   Diastereoselective synthesis of β-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-N-tert-butoxycarbonyl-D-alanine [J].
Lieberknecht, A ;
Griesser, H ;
Krämer, B ;
Bravo, RD ;
Colinas, PA ;
Grigera, RJ .
TETRAHEDRON, 1999, 55 (21) :6475-6482