Microwave-assisted synthesis of ethynylarylboronates for the construction of boronic acid-based fluorescent sensors for carbohydrates

被引：25
作者：
Zheng, SL
Reid, S
Lin, N
Wang, BH
机构：
[1] Georgia State Univ, Dept Chem, Atlanta, GA 30302 USA
[2] Georgia State Univ, Ctr Biotechnol & Drug Design, Atlanta, GA 30302 USA
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 14期
基金：
美国国家卫生研究院;
关键词：
ethynylaryl boronates; synthesis; Sonogashira; microwave irradiation;
D O I：
10.1016/j.tetlet.2006.02.012
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A reliable and operationally simple procedure for the synthesis of 2.2-dimethylpropane-1,3-diyl ethynylaryl boronates 4 was developed. The key step is microwave-facilitated selective formation of 2,2-dimethylpropane-1,3-diyl trimethylsilylethynylaryl boronates by Sonogashira reaction front the corresponding bromides. The use of microwave was found to significantly improve the reaction yield and shorten the reaction time. The 2,2-dimethylpropane-1,3-diyl ethynylaryl boronates 4 prepared can be used in the construction of diboronic acid libraries through [2+3] Huisgen cycloaddition for carbohydrate fluorescent sensor development. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2331 / 2335
页数：5
相关论文
共 57 条
[1]   Boronic acid fluorescent sensors for monosaccharide signaling based on the 6-methoxyquinolinium heterocyclic nucleus: progress toward noninvasive and continuous glucose monitoring [J].
Badugu, R ;
Lakowicz, JR ;
Geddes, CD .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (01) :113-119
[2]   SYNTHESIS OF A FLUORESCENT BORONIC ACID WHICH REVERSIBLY BINDS TO CELL-WALLS AND A DIBORONIC ACID WHICH AGGLUTINATES ERYTHROCYTES [J].
BURNETT, TJ ;
PEEBLES, HC ;
HAGEMAN, JH .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1980, 96 (01) :157-162
[3]   Fluorescent chemosensors for carbohydrates: A decade's worth of bright spies for saccharides in review [J].
Cao, HS ;
Heagy, MD .
JOURNAL OF FLUORESCENCE, 2004, 14 (05) :569-584
[4]   Highly fructose selective transport promoted by boronic acids based on a pentaerythritol core [J].
Draffin, SP ;
Duggan, PJ ;
Duggan, SAM .
ORGANIC LETTERS, 2001, 3 (06) :917-920
[5]   Rapid microwave promoted sonogashira coupling reactions on solid phase [J].
Erdélyi, M ;
Gogoll, A .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6431-6434
[6]   Rapid homogeneous-phase Sonogashira coupling reactions using controlled microwave heating [J].
Erdélyi, M ;
Gogoll, A .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) :4165-4169
[7]   A highly fluorescent water-soluble boronic acid reporter for saccharide sensing that shows ratiometric UV changes and significant fluorescence changes [J].
Gao, XM ;
Zhang, YL ;
Wang, BH .
TETRAHEDRON, 2005, 61 (38) :9111-9117
[8]   Naphthalene-based water-soluble fluorescent boronic acid isomers suitable for ratiometric and off-on sensing of saccharides at physiological pH [J].
Gao, XM ;
Zhang, YL ;
Wang, BH .
NEW JOURNAL OF CHEMISTRY, 2005, 29 (04) :579-586
[9]   New boronic acid fluorescent reporter compounds. 2. A naphthalene-based on-off sensor functional at physiological pH [J].
Gao, XM ;
Zhang, YL ;
Wang, BH .
ORGANIC LETTERS, 2003, 5 (24) :4615-4618
[10]   Preparation and screening of diboronate arrays for identification of carbohydrate binders [J].
Hoeg-Jensen, T .
QSAR & COMBINATORIAL SCIENCE, 2004, 23 (05) :344-351
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