Synthesis of a thio-linked analogue of sialyl Lewis X

被引：66

作者：

Eisele, T

Toepfer, A

Kretzschmar, G

Schmidt, RR

机构：

[1] UNIV KONSTANZ,FAK CHEM,D-78434 CONSTANCE,GERMANY

[2] HOECHST AG,ZENT FORSCH,D-65926 FRANKFURT,GERMANY

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 09期

关键词：

D O I：

10.1016/0040-4039(96)00061-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thiolinked sialyl Lewis X analogue 2 was obtained from neuraminic acid, D-galactose, and L-fucose. Galactose was transformed into 3-thiogalactose building block 6 and also into the required 3,4-dithioglucose moiety. Thioglycoside bond formation was performed via base-promoted S-glycosylation [Neu5Aca alpha(2-3S)Gal and Gal beta(1-4S)Glc linkages] and via acid catalyzed S-glycosylation [Fuca(1-3S)Glc and Glc beta-(1-1S)heptyl linkages].

引用

页码：1389 / 1392

页数：4

共 20 条

[1] BAR T, 1991, LIEBIGS ANN CHEM, P185
[2] A SIMPLE METHOD FOR THE PREPARATION OF THIOGLYCOSIDES OF N-ACETYLNEURAMINIC ACID
BENNETT, S
VONITZSTEIN, M
KIEFEL, MJ
[J]. CARBOHYDRATE RESEARCH, 1994, 259 (02) : 293 - 299
[3] ENDOTHELIAL LEUKOCYTE ADHESION MOLECULE-1 - AN INDUCIBLE RECEPTOR FOR NEUTROPHILS RELATED TO COMPLEMENT REGULATORY PROTEINS AND LECTINS
BEVILACQUA, MP
STENGELIN, S
GIMBRONE, MA
SEED, B
[J]. SCIENCE, 1989, 243 (4895) : 1160 - 1165
[4] APPLICATION OF GLYCALS TO THE SYNTHESIS OF OLIGOSACCHARIDES - CONVERGENT TOTAL SYNTHESES OF THE LEWIS-X TRISACCHARIDE SIALYL-LEWIS-X ANTIGENIC DETERMINANT AND HIGHER CONGENERS
DANISHEFSKY, SJ
GERVAY, J
PETERSON, JM
MCDONALD, FE
KOSEKI, K
GRIFFITH, DA
ORIYAMA, T
MARSDEN, SP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (07) : 1940 - 1953
[5] GEYER A, UNPUB
[6] STUDIES ON THE THIOGLYCOSIDES OF N-ACETYLNEURAMINIC ACID .1. SYNTHESIS OF ALKYL ALPHA-GLYCOSIDES OF 2-THIO-N-ACETYLNEURAMINIC ACID
HASEGAWA, A
NAKAMURA, J
KISO, M
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1986, 5 (01) : 11 - 19
[7] SYNTHETIC STUDIES ON SIALOGLYCOCONJUGATES .65. STEREOCONTROLLED SYNTHESIS OF POSITIONAL ISOMERS OF TUMOR-ASSOCIATED GANGLIOSIDE ANTIGENS, SIALYL-LEWIS-X AND SIALYL PARAGLOBOSIDE
HOTTA, K
ITOH, K
KAMEYAMA, A
ISHIDA, H
KISO, M
HASEGAWA, A
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1995, 14 (01) : 115 - 133
[8] SYNTHESIS OF BIOLOGICALLY-ACTIVE SIALYL-LEWIS-X MIMETICS
HUANG, HM
WONG, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) : 3100 - 3106
[9] A TOTAL SYNTHESIS OF GLYCONONAOSYL CERAMIDE WITH A SIALYL DIMERIC LE(X) SEQUENCE
IIDA, M
ENDO, A
FUJITA, S
NUMATA, M
MATSUZAKI, Y
SUGIMOTO, M
NUNOMURA, S
OGAWA, T
[J]. CARBOHYDRATE RESEARCH, 1995, 270 (02) : C15 - C19
[10] KAILA N, 1995, TETRAHEDRON LETT, V36, P5503

← 1 2 →