Stereoselectivity control in anomeric O-alkylation. Application to the synthesis of C-2 symmetric glycoconjugates.

被引：30

作者：

Lubineau, A

Escher, S

Alais, J

Bonnaffe, D

机构：

[1] Lab. Chim. Organique M., Inst. de Chim. Molec. d'Orsay, Université Paris Sud

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 23期

关键词：

D O I：

10.1016/S0040-4039(97)00830-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetrabutylammonium sits strongly influence the stereoselectivity of O-anomeric alkylation and allows to shift from beta to alpha selectivity. Allyl glucosaminide 7 prepared in this way, was used to synthesize the new type of C-2 symmetric neoglycoconjugates 1a-c. (C) 1997 Elsevier Science Ltd.

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页码：4087 / 4090

页数：4

相关论文

共 21 条

[1] DANTE-Z - A NEW APPROACH FOR ACCURATE FREQUENCY-SELECTIVITY USING HARD PULSES [J].

BOUDOT, D ;

CANET, D ;

BRONDEAU, J ;

BOUBEL, JC .

JOURNAL OF MAGNETIC RESONANCE, 1989, 83 (02) :428-439

[2] PSEUDO-3D NMR OF PROTEINS WITH SELECTIVE EXCITATION BY DANTE-Z - ONE-DIMENSIONAL TOCSY-NOESY EXPERIMENT [J].

BOUDOT, D ;

ROUMESTAND, C ;

TOMA, F ;

CANET, D .

JOURNAL OF MAGNETIC RESONANCE, 1990, 90 (01) :221-227

[3]

GRIMAUD JA, 1994, PATHOL RES PRACT, V190, P883

[4] RATIONAL DESIGN OF SYNTHETIC HEPARIN ANALOGS WITH TAILOR-MADE COAGULATION-FACTOR INHIBITORY ACTIVITY [J].

GROOTENHUIS, PDJ ;

WESTERDUIN, P ;

MEULEMAN, D ;

PETITOU, M ;

VANBOECKEL, CAA .

NATURE STRUCTURAL BIOLOGY, 1995, 2 (09) :736-739

[5] ANOMERIC O-ALKYLATION OF O-ACETYL-PROTECTED SUGARS [J].

KLOTZ, W ;

SCHMIDT, RR .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1994, 13 (08) :1093-1101

[6]

KLOTZ W, 1993, LIEBIGS ANN CHEM, P683

[7] SYNTHESIS OF 3-(2-AMINOETHYLTHIO)PROPYL GLYCOSIDES [J].

LEE, RT ;

LEE, YC .

CARBOHYDRATE RESEARCH, 1974, 37 (01) :193-201

[8] MOLECULAR-ORGANIZATION OF THE INTERFERON GAMMA-BINDING DOMAIN IN HEPARAN-SULFATE [J].

LORTAT-JACOB, H ;

TURNBULL, JE ;

GRIMAUD, JA .

BIOCHEMICAL JOURNAL, 1995, 310 :497-505

[9] SYNTHESES OF ALPHA-LINKED DERIVATIVES OF N-ACETYL GLUCOSAMINE AND GAL-BETA(1-3)GALNAC (T-ANTIGEN) DIRECTLY WITH THE NATURAL N-ACETYL PROTECTING GROUP [J].

LUBINEAU, A ;

BIENAYME, H ;

LEGALLIC, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (24) :1918-1919

[10] FGF BINDING AND FGF RECEPTOR ACTIVATION BY SYNTHETIC HEPARAN-DERIVED DISACCHARIDES AND TRISACCHARIDES [J].

ORNITZ, DM ;

HERR, AB ;

NILSSON, M ;

WESTMAN, J ;

SVAHN, CM ;

WAKSMAN, G .

SCIENCE, 1995, 268 (5209) :432-436