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Penta­fluoro­phenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azido­methyl-3,4-dimeth­oxy-2,3,4,5-tetra­hydro­furan-3-carboxamido]­meth­yl}-3,4-dimeth­oxy-2,3,4,5-tetra­hydro­furan-3-carboxyl­ate

The title compound, C(22)H(25)F(5)N(4)O(9), is a stable penta­fluoro­phenyl ester inter­mediate in the synthesis of novel homo-oligomeric structures containing branched carbon chains. The structure is epimeric to the previously characterized dimeric penta­fluoro­phenyl ester with stereochemistry (3R...

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Detalles Bibliográficos
Autores principales: Simone, Michela I., Edwards, Alison A., Parker, Samuel G., Tranter, George E., Fleet, George W. J., Watkin, David J.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3009349/
https://www.ncbi.nlm.nih.gov/pubmed/21588915
http://dx.doi.org/10.1107/S1600536810038559
Descripción
Sumario:The title compound, C(22)H(25)F(5)N(4)O(9), is a stable penta­fluoro­phenyl ester inter­mediate in the synthesis of novel homo-oligomeric structures containing branched carbon chains. The structure is epimeric to the previously characterized dimeric penta­fluoro­phenyl ester with stereochemistry (3R,4R,5R), which was synthesized using d-ribose as starting material. The crystal structure of the title mol­ecule removes any ambiguities arising from the relative stereochemistries of the six chiral centres. Two hydrogen bonds, bifurcating from the NH group, stabilize the crystal: one intra­molecular and one inter­molecular, both involving O atoms of the meth­oxy groups. The asymmetric unit contains two independent mol­ecules not related by any pseudo-symmetry operators. The major conformational differences are localized, leading to one mol­ecule being extended compared to the other. The collected crystal was twinned (twin ratio is 0.939:0.061), and the azide group is positionally disordered over two positions in one mol­ecule [occupancy ratio 0.511 (18):0.489 (18)].