A highly practical synthesis of sulfated Lewis X: One-pot, two-step glycosylation using ''armed/disarmed'' coupling and selective benzoylation and sulfation

被引：48

作者：

Tsukida, T ^{[1
]}

Yoshida, M ^{[1
]}

Kurokawa, K ^{[1
]}

Nakai, Y ^{[1
]}

Achiha, T ^{[1
]}

Kiyoi, T ^{[1
]}

Kondo, H ^{[1
]}

机构：

[1] KANEBO LTD,NEW DRUG RES LABS,DEPT MED CHEM,MIYAKOJIMA KU,OSAKA 534,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 20期

关键词：

D O I：

10.1021/jo970076m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In spite of the several attractive biological activities of the Le(x), sLe(x), and sulfated Le(x) derivatives, there are still limitations in their practical syntheses. One of the most difficult problems is the many steps required for their syntheses. Therefore, we investigated simple constructions of the Le(x) analogs and succeeded in establishing highly practical syntheses of the Le(x) and sulfated Le(x) analogs. Especially, the ''armed/disarmed'' method allowed the first synthesis of Le(x) derivatives by a one-pot, two-step glycosylation. This synthetic strategy could be an applicable and useful method for oligosaccharide constructions of Le(x), sulfated Le(x), and other derivatives.

引用

页码：6876 / 6881

页数：6

共 48 条

[1] IDENTIFICATION OF AN INDUCIBLE ENDOTHELIAL LEUKOCYTE ADHESION MOLECULE [J].

BEVILACQUA, MP ;

POBER, JS ;

MENDRICK, DL ;

COTRAN, RS ;

GIMBRONE, MA .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1987, 84 (24) :9238-9242

[2] DISPIROKETALS IN SYNTHESIS .5. A NEW OPPORTUNITY FOR OLIGOSACCHARIDE SYNTHESIS USING DIFFERENTIALLY ACTIVATED GLYCOSYL DONORS AND ACCEPTORS [J].

BOONS, GJ ;

GRICE, P ;

LESLIE, R ;

LEY, SV ;

YEUNG, LL .

TETRAHEDRON LETTERS, 1993, 34 (52) :8523-8526

[3] Strategies in oligosaccharide synthesis [J].

Boons, GJ .

TETRAHEDRON, 1996, 52 (04) :1095-1121

[4] THE SELECTIN FAMILY OF CARBOHYDRATE-BINDING PROTEINS - STRUCTURE AND IMPORTANCE OF CARBOHYDRATE LIGANDS FOR CELL-ADHESION [J].

CUMMINGS, RD ;

SMITH, DF .

BIOESSAYS, 1992, 14 (12) :849-856

[5] REMARKABLE REGIOSELECTIVITY IN THE CHEMICAL GLYCOSYLATION OF GLYCAL ACCEPTORS - A CONCISE SOLUTION TO THE SYNTHESIS OF SIALYL-LEWIS-X GLYCAL [J].

DANISHEFSKY, SJ ;

GERVAY, J ;

PETERSON, JM ;

MCDONALD, FE ;

KOSEKI, K ;

ORIYAMA, T ;

GRIFFITH, DA ;

WONG, CH ;

DUMAS, DP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8329-8331

[6] 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

[7] APPLICATION OF GLYCALS TO THE SYNTHESIS OF OLIGOSACCHARIDES - CONVERGENT TOTAL SYNTHESES OF THE LEWIS-X TRISACCHARIDE SIALYL-LEWIS-X ANTIGENIC DETERMINANT AND HIGHER CONGENERS [J].

DANISHEFSKY, SJ ;

GERVAY, J ;

PETERSON, JM ;

MCDONALD, FE ;

KOSEKI, K ;

GRIFFITH, DA ;

ORIYAMA, T ;

MARSDEN, SP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (07) :1940-1953

[8]

DASGUPTA F, 1994, EXPERT OPIN INV DRUG, V3, P709

[9] ENZYMATIC-SYNTHESIS OF SIALYL LEX AND DERIVATIVES BASED ON A RECOMBINANT FUCOSYL-TRANSFERASE [J].

DUMAS, DP ;

ICHIKAWA, Y ;

WONG, CH ;

LOWE, JB ;

NAIR, RP .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (08) :425-428

[10] ARMED-DISARMED EFFECTS IN GLYCOSYL DONORS - RATIONALIZATION AND SIDETRACKING [J].

FRASERREID, B ;

WU, ZF ;

UDODONG, UE ;

OTTOSSON, H .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6068-6070

← 1 2 3 4 5 →