Recent developments in glycosyl urea synthesis

作者: Matthew J. McKay , Hien M. Nguyen

DOI: 10.1016/J.CARRES.2013.08.007

关键词:

摘要: The area of sugar urea derivatives has received considerable attention in recent years because the unique structural properties and activities that these compounds display. urea-linkage at anomeric center is a robust alternative to naturally occurring O- N-glycosidic linkages oligosaccharides glycoconjugates, natural products have been identified contain structures show remarkable biological activity. While methods for installing β-urea-linkage around decades, first synthesis α-urea glycosides much more recent. In either case, selective glycosyl ureas can be quite challenging, mixture α- β-isomers will often result. This paper provide comprehensive review synthetic approaches β-urea examine structure activity their analogues them.

参考文章(76)
Daisuke Sawada, Shinya Sasayama, Hideyo Takahashi, Shiro Ikegami, A new and facile synthesis of carbamate- and urea-linked glycoconjugate using modified Curtius rearrangement Tetrahedron Letters. ,vol. 47, pp. 7219- 7223 ,(2006) , 10.1016/J.TETLET.2006.07.139
RANDAL H. CHEN, DAVID N. WHITTERN, ALEXANDER M. BUKO, JAMES B. MCALPINE, Coumamidines, new broad spectrum antibiotics of the cinodine type. II. Isolation and structural elucidation. The Journal of Antibiotics. ,vol. 42, pp. 533- 537 ,(1989) , 10.7164/ANTIBIOTICS.42.533
José G. Fernández-Bolaños, Óscar López, Heterocycles from Carbohydrate Isothiocyanates Springer Berlin Heidelberg. pp. 67- 100 ,(2006) , 10.1007/7081_2007_052
Tomoya OGAWA, Satoru NAKABAYASHI, Seiichi SHIBATA, Synthetic Studies on Nephritogenic Glycosides. Synthesis of N-(β-l-Aspartyl)-α-d-glucopyranosylamine Agricultural and biological chemistry. ,vol. 47, pp. 281- 285 ,(1983) , 10.1271/BBB1961.47.281
Takeo Naito, Miyoshi Hirata, Tomoyoshi Kawakami, Mitsuji Sano, Studies on Nucleosides and Nucleotides. I. Synthesis of Glycosylthymines from Glycosylureas. Chemical & Pharmaceutical Bulletin. ,vol. 9, pp. 703- 708 ,(1961) , 10.1248/CPB.9.703
Abigail G. Doyle, Eric N. Jacobsen, Small-molecule H-bond donors in asymmetric catalysis. Chemical Reviews. ,vol. 107, pp. 5713- 5743 ,(2007) , 10.1021/CR068373R
Yoshiyasu Ichikawa, Yohei Matsukawa, Minoru Isobe, Synthesis of urea-tethered neoglycoconjugates and pseudooligosaccharides in water. Journal of the American Chemical Society. ,vol. 128, pp. 3934- 3938 ,(2006) , 10.1021/JA056253F
Yoshiyasu Ichikawa, Yohei Matsukawa, Mari Tamura, Fumiyo Ohara, Minoru Isobe, Hiyoshizo Kotsuki, Synthesis of urea-tethered disaccharides in water. Chemistry-an Asian Journal. ,vol. 1, pp. 717- 723 ,(2006) , 10.1002/ASIA.200600190
M. H. Benn, A. S. Jones, 761. Glycosylureas. Part I. Preparation and some reactions of D-glucosylureas and D-ribosylureas Journal of The Chemical Society (resumed). pp. 3837- 3841 ,(1960) , 10.1039/JR9600003837
Juan Manuel Benito, Carmen Ortiz Mellet, Kashinath Sadalapure, Thisbe K Lindhorst, Jacques Defaye, José Manuel Garcı́a Fernández, None, Synthesis and anomeric stability of (1→6)-thiourea-linked pseudooligosaccharides Carbohydrate Research. ,vol. 320, pp. 37- 48 ,(1999) , 10.1016/S0008-6215(99)00141-X