Optimization of glycosylation reactions in a microreactor

被引:46
作者
Geyer, Karolin [1 ]
Seeberger, Peter H. [1 ]
机构
[1] ETH, Swiss Fed Inst Technol, Organ Chem Lab, CH-8093 Zurich, Switzerland
关键词
D O I
10.1002/hlca.200790046
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Glycosylations are notoriously difficult reactions that require extensive optimization regarding the type of anomeric leaving group, solvent, reaction temperature, and reaction time. Described is the use of a silicon-based microreactor to screen reaction conditions and to scale-up synthetic procedures. For the first time, glycosyl phosphates were employed in a microreactor. The optimized reaction conditions were successfully transferred to a batch process.
引用
收藏
页码:395 / 403
页数:9
相关论文
共 34 条
[1]  
Ali A, 2005, CHEM COMMUN, P1224
[2]   N-pentenyl glycoside methodology in the stereoselective construction of the tetrasaccharyl cap portion of Leishmania lipophosphoglycan [J].
Arasappan, A ;
FraserReid, B .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2401-2406
[3]   Stereoselective synthesis of allyl-C-mannosyl compounds:: Use of a temporary silicon connection in intramolecular allylation strategies with allylsilanes [J].
Beignet, J ;
Tiernan, J ;
Woo, CH ;
Kariuki, BM ;
Cox, LR .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (19) :6341-6356
[4]   Miniaturized continuous flow reaction vessels: influence on chemical reactions [J].
Brivio, M ;
Verboom, W ;
Reinhoudt, DN .
LAB ON A CHIP, 2006, 6 (03) :329-344
[5]   Rapid protein digestion and identification using monolithic enzymatic microreactor coupled with nano-liquid chromatography-electro spray ionization mass spectrometry [J].
Duan, JC ;
Sun, LL ;
Liang, Z ;
Zhang, J ;
Wang, H ;
Zhang, LH ;
Zhang, WB ;
Zhang, YK .
JOURNAL OF CHROMATOGRAPHY A, 2006, 1106 (1-2) :165-174
[6]  
Ehrfeld W., 2000, Microreactors: new technology for modern chemistry, DOI DOI 10.1002/3527601953
[7]   Micro reactors: principles and applications in organic synthesis [J].
Fletcher, PDI ;
Haswell, SJ ;
Pombo-Villar, E ;
Warrington, BH ;
Watts, P ;
Wong, SYF ;
Zhang, XL .
TETRAHEDRON, 2002, 58 (24) :4735-4757
[8]   Microreactor synthesis of β-peptides [J].
Floegel, Oliver ;
Codee, Jeroen D. C. ;
Seebach, Dieter ;
Seeberger, Peter H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (42) :7000-7003
[9]   Microreactors as tools for synthetic chemists -: The chemists' round-bottomed flask of the 21st century? [J].
Geyer, Karolin ;
Codee, Jeroen D. C. ;
Seeberger, Peter H. .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (33) :8434-8442
[10]   A microfluidic device for kinetic optimization of protein crystallization and in situ structure determination [J].
Hansen, CL ;
Classen, S ;
Berger, JM ;
Quake, SR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (10) :3142-3143