Synthesis of a potent antagonist of E-selectin

被引：19

作者：

Hanessian, S ^{[1
]}

Mascitti, V ^{[1
]}

Rogel, O ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 10期

关键词：

D O I：

10.1021/jo0110956

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of an antagonist of E-selectin previously reported by a group at Novartis Pharma in Basel is described. An important feature involves the formation of an ether linkage based on a Rh-II-catalyzed reaction. Stereocontrolled glycosylations rely on the anomeric activation of 2-pyridylthio carbonate as leaving group for the attachment of beta-D-galactopyranosyl and alpha-L-fucopyranosyl units on a common 1,5-anhydro D-glucitol scaffold.

引用

页码：3346 / 3354

页数：9

共 90 条

[1] RHODIUM (II) CATALYZED-REACTIONS OF DIAZO-CARBONYL COMPOUNDS [J].

ADAMS, J ;

SPERO, DM .

TETRAHEDRON, 1991, 47 (10-11) :1765-1808

[2] TETRAFLUOROBORIC ACID, AN EFFICIENT CATALYST IN CARBOHYDRATE PROTECTION AND DEPROTECTION REACTIONS [J].

ALBERT, R ;

DAX, K ;

PLESCHKO, R ;

STUTZ, AE .

CARBOHYDRATE RESEARCH, 1985, 137 (MAR) :282-290

[3] THE SYNTHESIS OF NOVEL MIMICS OF THE SIALYL-LEWIS-X DETERMINANT [J].

ALLANSON, NM ;

DAVIDSON, AH ;

FLOYD, CD ;

MARTIN, FM .

TETRAHEDRON-ASYMMETRY, 1994, 5 (11) :2061-2076

[4] LIFETIME OF THE P-SELECTIN-CARBOHYDRATE BOND AND ITS RESPONSE TO TENSILE FORCE IN HYDRODYNAMIC FLOW [J].

ALON, R ;

HAMMER, DA ;

SPRINGER, TA .

NATURE, 1995, 374 (6522) :539-542

[5]

[Anonymous], [No title captured]

[6] COMPARISON OF A PROTEIN MODEL WITH ITS X-RAY STRUCTURE - THE LIGAND-BINDING DOMAIN OF E-SELECTIN [J].

BAJORATH, J ;

STENKAMP, R ;

ARUFFO, A .

BIOCONJUGATE CHEMISTRY, 1995, 6 (01) :3-6

[7] SYNTHESIS AND STRUCTURAL-ANALYSIS USING 2-D NMR OF SIALYL LEWIS-X (SLE(X)) AND LEWIS-X (LE(X)) OLIGOSACCHARIDES - LIGANDS RELATED TO E-SELECTIN [ELAM-1] BINDING [J].

BALL, GE ;

ONEILL, RA ;

SCHULTZ, JE ;

LOWE, JB ;

WESTON, BW ;

NAGY, JO ;

BROWN, EG ;

HOBBS, CJ ;

BEDNARSKI, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5449-5451

[8] Synthesis and biological activity of conformationally constrained sialyl Lewis X analogues with reduced carbohydrate character. [J].

Bamford, MJ ;

Bird, M ;

Gore, PM ;

Holmes, DS ;

Priest, R ;

Prodger, JC ;

Saez, V .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (03) :239-244

[9]

BEVILACQUA MP, 1993, ANNU REV IMMUNOL, V11, P767, DOI 10.1146/annurev.iy.11.040193.004003

[10] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].

BLANCHETTE, MA ;

CHOY, W ;

DAVIS, JT ;

ESSENFELD, AP ;

MASAMUNE, S ;

ROUSH, WR ;

SAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186

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