One-pot multicomponent synthesis of 2,3-dihydropyrans: new access to furanose-pyranose 1,3-C-C-linked-disaccharides

被引：27

作者：

Castagnolo, Daniele ^{[1
]}

Botta, Lorenzo ^{[1
]}

Botta, Maurizio ^{[1
]}

机构：

[1] Univ Siena, Dipartimento Farmaco Chim Tecnol, I-53100 Siena, Italy

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 14期

关键词：

Enyne metathesis; Hetero-Diels-Alder; Multicomponent reaction; Dihydropyrans; Disaccharide; C-DISACCHARIDE; METATHESIS; ALDEHYDES; PRODUCTS; ROUTES;

D O I：

10.1016/j.tetlet.2009.01.047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficent synthesis of 2,3-dihydropyrans from different terminal alkynes was developed. The 2,3-dihydropyrans were obtained in a few minutes through a microwave-assisted multicomponent enyne cross-metathesis/hetero-Diels-Alder reaction. Starting from C-ethynyl-ribofuranose, a new multicomponent approach to furanose-pyramose 1,3-C-C-linked disaccharides was also developed. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：1526 / 1528

页数：3

共 26 条

[1] SYNTHESIS OF ALPHA-METHYL 1',2'-DIDEOXYCELLOBIOSIDE - A NOVEL C-DISACCHARIDE [J].

ARMSTRONG, RW ;

TEEGARDEN, BR .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :915-922

[2] Thermal/hyperbaric heterocycloaddition of 1,4-dialkoxy-1,3-dienes:: The de novo (E,Z) way to sugars [J].

Bataille, C ;

Bégin, G ;

Guillam, A ;

Lemiègre, L ;

Lys, C ;

Maddaluno, J ;

Toupet, L .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (23) :8054-8062

[3] Diels-Alder reactions of (Z)-ethyl 3-[(1-ethoxycarbonyloxy-2-methoxy)ethenyl]-2-(ethoxycarbonyloxy)indole-1-carboxylate. Synthesis of the carbazole alkaloid carbazomycin B [J].

Beccalli, EM ;

Marchesini, A ;

Pilati, T .

TETRAHEDRON, 1996, 52 (08) :3029-3036

[4]

Bertozzi C., 1996, FRONT NAT PROD RES, V1, P316

[5] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS [J].

BOIVIN, TLB .

TETRAHEDRON, 1987, 43 (15) :3309-3362

[6] Microwave-assisted ethylene-alkyne cross-metathesis:: synthesis of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes [J].

Castagnolo, D ;

Renzulli, ML ;

Galletti, E ;

Corelli, F ;

Botta, M .

TETRAHEDRON-ASYMMETRY, 2005, 16 (17) :2893-2896

[7] Practical syntheses of enantiomerically pure N-acetylbenzhydrylamines [J].

Castagnolo, Daniele ;

Giorgi, Gianluca ;

Spinosa, Raffaella ;

Corelli, Federico ;

Botta, Maurizio .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (22) :3676-3686

[8] THE PSEUDOMONIC ACIDS [J].

CLASS, YJ ;

DESHONG, P .

CHEMICAL REVIEWS, 1995, 95 (06) :1843-1857

[9] LEWIS ACID MEDIATED CONDENSATION OF ALKENOLS AND ALDEHYDES - A SELECTIVE SYNTHESIS OF TETRAHYDROPYRANS AND OXEPANES [J].

COPPI, L ;

RICCI, A ;

TADDEI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (04) :911-913

[10] Formylation of carbohydrates and the evolution of synthetic routes to artificial oligosaccharides and glycoconjugates [J].

Dondoni, A .

PURE AND APPLIED CHEMISTRY, 2000, 72 (09) :1577-1588

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