Chemical synthesis of oligosaccharides: Efficiency and selectivity

被引：6

作者：

Kanie, O ^{[1
]}

Ogawa, T ^{[1
]}

Ito, Y ^{[1
]}

机构：

[1] RIKEN, Inst Phys & Chem Res, Wako, Saitama 3510198, Japan

来源：

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 1998年 / 56卷 / 11期

关键词：

D O I：

10.5059/yukigoseikyokaishi.56.952

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Due to high demand to access biologically important oligosaccharide structures, efficient and stereoselective synthetic methods are required. This article addresses these two issues from our recent studies. The first part deals with P-mannosylation and cr-sialylation known as the two most difficult glycosylation reactions which were now made possible by means of an "intramolecular aglycon delivery" system and control by "auxiliary", respectively. In the second part, the remarkably efficient "orthogonal glycosylation strategy" which was developed based on tactical analysis of oligosaccharide synthesis is described.

引用

页码：952 / 962

页数：11

共 86 条

[11]

DAN A, IN PRESS CHEM EUR J

[12] POLYMER-SUPPORTED SOLUTION SYNTHESIS OF OLIGOSACCHARIDES USING A NOVEL VERSATILE LINKER FOR THE SYNTHESIS OF D-MANNOPENTAOSE, A STRUCTURAL UNIT OF D-MANNANS OF PATHOGENIC YEASTS [J].

DOUGLAS, SP ;

WHITFIELD, DM ;

KREPINSKY, JJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (07) :2116-2117

[13] Glycobiology: Toward understanding the function of sugars [J].

Dwek, RA .

CHEMICAL REVIEWS, 1996, 96 (02) :683-720

[14] A NEW N-ACETYLNEURAMINIC ACID DONOR FOR HIGHLY STEREOSELECTIVE ALPHA-SIALYLATION [J].

ERCEGOVIC, T ;

MAGNUSSON, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (07) :831-832

[15]

FLITSCH SL, 1997, GLYCOPEPTIDES RELATE, P207

[16] ON THE CONTROLLED OXIDATIVE COUPLING OF GLYCALS - A NEW STRATEGY FOR THE RAPID ASSEMBLY OF OLIGOSACCHARIDES [J].

FRIESEN, RW ;

DANISHEFSKY, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6656-6660

[17] THIOGLYCOSIDES AS GLYCOSYLATING AGENTS IN OLIGOSACCHARIDE SYNTHESIS [J].

FUGEDI, P ;

GAREGG, PJ ;

LONN, H ;

NORBERG, T .

GLYCOCONJUGATE JOURNAL, 1987, 4 (02) :97-108

[18]

Fukuda M., 1994, MOL GLYCOBIOLOGY

[19] PARA-ANISYL GROUP - A VERSATILE PROTECTING GROUP FOR PRIMARY ALCOHOLS [J].

FUKUYAMA, T ;

LAIRD, AA ;

HOTCHKISS, LM .

TETRAHEDRON LETTERS, 1985, 26 (51) :6291-6292

[20] SACCHARIDES OF BIOLOGICAL IMPORTANCE - CHALLENGES AND OPPORTUNITIES FOR ORGANIC-SYNTHESIS [J].

GAREGG, PJ .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (12) :575-580

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