Synthesis of sugar-based ethenyl ethers through a vinyl bis-sulfone methodology

被引：21

作者：

Chéry, F

Desroses, M

Tatibouët, A

De Lucchi, O

Rollin, P

机构：

[1] Univ Orleans, CNRS, UMR 6005, Inst Chim Organ & Analyt, F-45067 Orleans, France

[2] Univ Venice, Dipartimento Chim, I-30123 Venice, Italy

来源：

TETRAHEDRON | 2003年 / 59卷 / 25期

关键词：

carbohydrates; alkoxyvinylsulfones; ethenyl ethers; desulfonylation;

D O I：

10.1016/S0040-4020(03)00661-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The recently devised route to ethenyl ethers-i.e. 1,2-bis(phenylsulfonyl)ethylene (BPSE)-mediated conversion of alcohols into beta-alkoxyvinyl sulfones followed by reductive desulfonylation-has been applied in the carbohydrate field to the synthesis of a number of vinyl-functionalised monosaccharides, a number of which had not been prepared via alternative routes. (C) 2003 Elsevier Science Ltd. All rights reserved.

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页码：4563 / 4572

页数：10

相关论文

共 42 条

[1] Ti(IV) promoted 1,3-dipolar cycloaddition of nitrones to vinyl ethers [J].

Bayón, P ;

de March, P ;

Figueredo, M ;

Font, J .

TETRAHEDRON, 1998, 54 (51) :15691-15700

[2] CYCLOADDITION OF NITRILE OXIDES TO HOMOCHIRAL VINYL ETHERS [J].

BOA, AN ;

BOOTH, SE ;

DAWKINS, DA ;

JENKINS, PR ;

FAWCETT, J ;

RUSSELL, DR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (12) :1277-1278

[3] CYCLOADDITION OF NITRILE OXIDES TO HOMOCHIRAL VINYL ETHERS [J].

BOA, AN ;

DAWKINS, DA ;

HERGUETA, AR ;

JENKINS, PR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (08) :953-960

[4] Vinyl glycosides in oligosaccharide synthesis .2. The use of allyl and vinyl glycosides in oligosaccharide synthesis [J].

Boons, GJ ;

Isles, S .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4262-4271

[5] Vinyl glycosides in oligosaccharide synthesis: A strategy for the preparation of trisaccharide libraries based on latent-active glycosylation [J].

Boons, GJ ;

Heskamp, B ;

Hout, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (23-24) :2845-2847

[6]

Cabianca E, 2001, SYNLETT, P1962

[7]

CHOUDURY A, 1989, TETRAHEDRON LETT, V37, P4921

[8]

Clark JS, 1999, TETRAHEDRON, V55, P8231

[9]

COTTIER L, 1979, SYNTHESIS-STUTTGART, P711

[10] Synthesis of 2-CF3-tetrahydroquinoline and quinoline derivatives from CF3-N-aryl-aldimine [J].

Crousse, B ;

Bégué, JP ;

Bonnet-Delpon, D .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :5009-5013

← 1 2 3 4 5 →