A novel sulfonamidoglycosylation of glycals

被引：50

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

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 23期

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

页码：4509 / 4511

页数：3

共 17 条

[1] A novel direct route to 2-deoxy-2-fluoro-aldoses and their corresponding derivatives
Albert, M
Dax, K
Ortner, J
[J]. TETRAHEDRON, 1998, 54 (19) : 4839 - 4848
[2] DIRECT PREPARATION OF 2-DEOXY-D-GLUCOPYRANOSIDES FROM GLUCALS WITHOUT FERRIER REARRANGEMENT
BOLITT, V
MIOSKOWSKI, C
LEE, SG
FALCK, JR
[J]. 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
DANISHEFSKY, SJ
BEHAR, V
RANDOLPH, JT
LLOYD, KO
[J]. 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
DANISHEFSKY, SJ
KOSEKI, K
GRIFFITH, DA
GERVAY, J
PETERSON, JM
MCDONALD, FE
ORIYAMA, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) : 8331 - 8333
[6] Cyclooxygenase inhibitors - current status and future prospects
Dannhardt, G
Kiefer, W
[J]. 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
GRIFFITH, DA
DANISHEFSKY, SJ
[J]. 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
Lieberknecht, A
Griesser, H
Krämer, B
Bravo, RD
Colinas, PA
Grigera, RJ
[J]. TETRAHEDRON, 1999, 55 (21) : 6475 - 6482

← 1 2 →