Sweet (hetero)aromatics: glycosylated templates for the construction of saccharide mimetics

被引：34
作者：
Wiebe, Christine [1 ,2 ]
Schlemmer, Claudine [1 ,2 ]
Weck, Stefan [1 ,2 ]
Opatz, Till [1 ]
机构：
[1] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55128 Mainz, Germany
[2] Univ Hamburg, Dept Chem, D-20146 Hamburg, Germany
来源：
CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 32期
关键词：
STEREOSELECTIVE-SYNTHESIS; ADHESION MOLECULES; ETHYLENE ISOSTERES; ALPHA-GLYCOSYL; DERIVATIVES; CYCLOADDITION; CONFORMATION; SELECTINS; LIGANDS; ALKYNES;
D O I：
10.1039/c1cc13078a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Mono- and diglycosylated aromatics and heteroaromatics may serve as building blocks for the construction of metabolically stable mimetics of oligosaccharides. Methods for their preparation from monosaccharidic precursors by direct C-glycosylation, dipolar cycloaddition or Larock cyclization are described.
引用
收藏
页码：9212 / 9214
页数：3
相关论文
共 55 条
[21]  
KUNZ H, 1991, LIEBIGS ANN CHEM, P649
[22]   SELECTINS - INTERPRETERS OF CELL-SPECIFIC CARBOHYDRATE INFORMATION DURING INFLAMMATION [J].
LASKY, LA .
SCIENCE, 1992, 258 (5084) :964-969
[23]   Inhibitory effects of glycosides from the leaves of Melaleuca quinquenervia on vascular contraction of rats [J].
Lee, TH ;
Wang, GJ ;
Lee, CK ;
Kuo, YH ;
Chou, CH .
PLANTA MEDICA, 2002, 68 (06) :492-496
[24]   Aryl C-glycosylation of phenols with glycosyl trifluoroacetimidates [J].
Li, Yuwen ;
Wei, Guo ;
Yu, Biao .
CARBOHYDRATE RESEARCH, 2006, 341 (16) :2717-2722
[25]  
LO CM, 2011, CHEM COMMUN, V47, P1240
[26]  
MAHLING JA, 1993, SYNTHESIS-STUTTGART, P325
[27]   Toward synthesis of novel C-glycoprotein from human RNase; Unexpected stereochemistry of epoxide opening reaction by organolithium reagents in the presence of Lewis acid [J].
Manabe, S ;
Ito, Y ;
Ogawa, T .
CHEMISTRY LETTERS, 1998, (09) :919-920
[28]   NEW APPROACH TO C-ARYL GLYCOSIDES STARTING FROM PHENOL AND GLYCOSYL FLUORIDE - LEWIS ACID-CATALYZED REARRANGEMENT OF O-GLYCOSIDE TO C-GLYCOSIDE [J].
MATSUMOTO, T ;
KATSUKI, M ;
SUZUKI, K .
TETRAHEDRON LETTERS, 1988, 29 (52) :6935-6938
[29]  
Melnik SY, 1996, BIOORG KHIM+, V22, P832
[30]   Synthesis and biological evaluation of oxindoles and benzimidazolinones derivatives [J].
Messaoudi, S ;
Sancelme, M ;
Polard-Housset, V ;
Aboab, B ;
Moreau, P ;
Prudhomme, M .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2004, 39 (05) :453-458
123456