Improved Synthesis of C2 and C6 Monoderivatives of α- and β-Cyclodextrin via the Click Chemistry Approach

被引：8

作者：

Chmurski, Kazimierz ^{[1
]}

Stepniak, Pawel ^{[1
,2
]}

Jurczak, Janusz ^{[2
]}

机构：

[1] Univ Warsaw, Fac Chem, PL-02093 Warsaw, Poland

[2] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 13期

关键词：

cyclodextrins; azides; copper; cycloaddition; ligands;

D O I：

10.1055/s-0034-1380701

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient multigram-scale azide-alkyne coupling of cyclodextrin derivatives mono-6-azido-6-deoxy--cyclodextrin, mono-2-O-propargyl--cyclodextrin, and mono-2-O-propargyl--cyclodextrin with terminal alkynyl aryl ethers or azides, mediated by copper(I) is reported. This process uses a stoichiometric ratio of substrates and 5 mol% of the copper catalyst to give the products with full conversion; thus, no chromatographic purification is necessary. The yields of both - and -cyclodextrin derivatives are in the range of 80 to 99%.

引用

收藏

页码：1838 / 1843

页数：6

相关论文

共 15 条

[1] β-Cyclodextrin as a mimetic of the natural GFP-chromophore environment [J].

Cacciarini, Martina ;

Nielsen, Mogens Brondsted ;

de Castro, Elisa Martinez ;

Marinescu, Lavinia ;

Bols, Mikael .

TETRAHEDRON LETTERS, 2012, 53 (08) :973-976

[2] Synthesis of β-cydodextrin derivatives functionalized with azobenzene [J].

Casas-Solvas, Juan M. ;

Martos-Maldonado, Manuel C. ;

Vargas-Berenguel, Antonio .

TETRAHEDRON, 2008, 64 (48) :10919-10923

[3] Ferrocene-β-Cyclodextrin Conjugates: Synthesis, Supramolecular Behavior, and Use as Electrochemical Sensors [J].

Casas-Solvas, Juan M. ;

Ortiz-Salmeron, Emilia ;

Fernandez, Ignacio ;

Garcia-Fuentes, Luis ;

Santoyo-Gonzalez, Francisco ;

Vargas-Berenguel, Antonio .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (33) :8146-8162

[4] Ultrasound-Promoted Copper-Catalyzed Azide-Alkyne Cycloaddition [J].

Cravotto, Giancarlo ;

Fokin, Valery V. ;

Garella, Davide ;

Binello, Arianna ;

Boffa, Luisa ;

Barge, Alessandro .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (01) :13-15

[5] When Cyclodextrins Meet Click Chemistry [J].

Faugeras, Pierre-Antoine ;

Boens, Benjamin ;

Elchinger, Pierre-Henri ;

Brouillette, Francois ;

Montplaisir, Daniel ;

Zerrouki, Rachida ;

Lucas, Romain .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (22) :4087-4105

[6] β-Cyclodextrin-Glycerol Dimers: Synthesis and NMR Conformational Analysis [J].

Legros, Vanessa ;

Vanhaverbeke, Cecile ;

Souard, Florence ;

Len, Christophe ;

Desire, Jerome .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (13) :2583-2590

[7] Molecular binding thermodynamics of spherical guests by β-cyclodextrins bearing aromatic substituents [J].

Li, Nan ;

Chen, Yong ;

Zhang, Ying-Ming ;

Wang, Li-Hua ;

Mao, Wen-Zhao ;

Liu, Yu .

THERMOCHIMICA ACTA, 2014, 576 :18-26

[8] Unusual Inversion Phenomenon of β-Cyclodextrin Dimers in Water [J].

Menuel, Stephane ;

Azaroual, Nathalie ;

Landy, David ;

Six, Natacha ;

Hapiot, Frederic ;

Monflier, Eric .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (14) :3949-3955

[9] PREPARATION OF ESTERS OF CARBOXYLIC AND PHOSPHORIC ACID VIA QUATERNARY PHOSPHONIUM SALTS [J].

MITSUNOBU, O ;

YAMADA, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1967, 40 (10) :2380-+

[10] Easily Accessible Mono- and Polytopic β-Cyclodextrin Hosts by Click Chemistry [J].

Mourer, Maxime ;

Hapiot, Frederic ;

Tilloy, Sebastien ;

Monflier, Eric ;

Menuel, Stephane .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (34) :5723-5730