104875-55-0Relevant academic research and scientific papers
A Convenient Route to Peracetylated 3-Deoxy-3-fluoro Analogues of d -Glucosamine and d -Galactosamine from a ?erny Epoxide
Karban, Jind?ich,Horník, ?těpán,?ervenková ??astná, Lucie,Sykora, Jan
, p. 1253 - 1256 (2014)
Peracetylated 3-deoxy-3-fluoro analogues of d-glucosamine and d-galactosamine 3 and 4, respectively, were prepared from 1,6:2,3-dianhydro-4-O- benzyl-β-d-mannopyranose (6). Azidolysis of 6 followed by reaction with diethylaminosulfur trifluoride gave 1,6-
Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine
Horník, ?těpán,?t'astná, Lucie ?ervenková,Cu?ínová, Petra,Sykora, Jan,Káňová, Kate?ina,Hrstka, Roman,Císa?ová, Ivana,Dra?ínsky, Martin,Karban, Jind?ich
supporting information, p. 750 - 759 (2016/07/06)
Background: Derivatives of D-glucosamine and D-galactosamine represent an important family of the cell surface glycan components and their fluorinated analogs found use as metabolic inhibitors of complex glycan biosynthesis, or as probes for the study of protein-carbohydrate interactions. This work is focused on the synthesis of acetylated 3-deoxy-3-fluoro, 4-deoxy-4-fluoro and 3,4-dideoxy-3,4-difluoro analogs of D-glucosamine and D-galactosamine via 1,6-anhydrohexopyranose chemistry. Moreover, the cytotoxicity of the target compounds towards selected cancer cells is determined. Results: Introduction of fluorine at C-3 was achieved by the reaction of 1,6-anhydro-2-azido-2-deoxy-4-O-benzyl-β-D-glucopyranose or its 4-fluoro analog with DAST. The retention of configuration in this reaction is discussed. Fluorine at C-4 was installed by the reaction of 1,6:2,3-dianhydro-β-D-talopyranose with DAST, or by fluoridolysis of 1,6:3,4-dianhydro-2-azido-β-D-galactopyranose with KHF2. The amino group was introduced and masked as an azide in the synthesis. The 1-O-deacetylated 3-fluoro and 4-fluoro analogs of acetylated D-galactosamine inhibited proliferation of the human prostate cancer cell line PC-3 more than cisplatin and 5-fluorouracil (IC50 28 ± 3 μM and 54 ± 5 μM, respectively). Conclusion: A complete series of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine is now accessible by 1,6-anhydrohexopyranose chemistry. Intermediate fluorinated 1,6-anhydro-2-azido-hexopyranoses have potential as synthons in oligosaccharide assembly.
Chiral Synthons for the Total Synthesis of Fluoro Amino Acids and Fluoro Analogues of Antibiotic Sugars
Faghih, Ramine,Escribano, Francisca Cabrera,Castillon, Sergio,Gracia, Jordi,Lukacs, Gabor,et al.
, p. 4558 - 4564 (2007/10/02)
Configurationally different 3-azido-2,3-dideoxy-2-fluoro and 2-azido-2,3-dideoxy-3-fluoro sugars, synthetic precursors of biologically important fluoro amino acids, were synthesized.Axial alcohols involved in vicinal diaxial systems undergo fluorodehydrox
