Penta-fluoro-phenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azido-methyl-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxamido]-meth-yl}-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxyl-ate.
The title compound, C(22)H(25)F(5)N(4)O(9), is a stable penta-fluoro-phenyl ester inter-mediate in the synthesis of novel homo-oligomeric structures containing branched carbon chains. The structure is epimeric to the previously characterized dimeric penta-fluoro-phenyl ester with stereochemistry (3R...
| Main Authors: | , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2010
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| _version_ | 1826263216569712640 |
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| author | Simone, M Edwards, A Parker, S Tranter, G Fleet, G Watkin, D |
| author_facet | Simone, M Edwards, A Parker, S Tranter, G Fleet, G Watkin, D |
| author_sort | Simone, M |
| collection | OXFORD |
| description | The title compound, C(22)H(25)F(5)N(4)O(9), is a stable penta-fluoro-phenyl ester inter-mediate in the synthesis of novel homo-oligomeric structures containing branched carbon chains. The structure is epimeric to the previously characterized dimeric penta-fluoro-phenyl ester with stereochemistry (3R,4R,5R), which was synthesized using d-ribose as starting material. The crystal structure of the title mol-ecule 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 intra-molecular and one inter-molecular, both involving O atoms of the meth-oxy groups. The asymmetric unit contains two independent mol-ecules not related by any pseudo-symmetry operators. The major conformational differences are localized, leading to one mol-ecule 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 mol-ecule [occupancy ratio 0.511 (18):0.489 (18)]. |
| first_indexed | 2024-03-06T19:48:12Z |
| format | Journal article |
| id | oxford-uuid:2310cbaa-8e7f-4d15-9eec-327734dbce01 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T19:48:12Z |
| publishDate | 2010 |
| record_format | dspace |
| spelling | oxford-uuid:2310cbaa-8e7f-4d15-9eec-327734dbce012022-03-26T11:42:11ZPenta-fluoro-phenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azido-methyl-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxamido]-meth-yl}-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxyl-ate.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:2310cbaa-8e7f-4d15-9eec-327734dbce01EnglishSymplectic Elements at Oxford2010Simone, MEdwards, AParker, STranter, GFleet, GWatkin, DThe title compound, C(22)H(25)F(5)N(4)O(9), is a stable penta-fluoro-phenyl ester inter-mediate in the synthesis of novel homo-oligomeric structures containing branched carbon chains. The structure is epimeric to the previously characterized dimeric penta-fluoro-phenyl ester with stereochemistry (3R,4R,5R), which was synthesized using d-ribose as starting material. The crystal structure of the title mol-ecule 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 intra-molecular and one inter-molecular, both involving O atoms of the meth-oxy groups. The asymmetric unit contains two independent mol-ecules not related by any pseudo-symmetry operators. The major conformational differences are localized, leading to one mol-ecule 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 mol-ecule [occupancy ratio 0.511 (18):0.489 (18)]. |
| spellingShingle | Simone, M Edwards, A Parker, S Tranter, G Fleet, G Watkin, D Penta-fluoro-phenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azido-methyl-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxamido]-meth-yl}-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxyl-ate. |
| title | Penta-fluoro-phenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azido-methyl-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxamido]-meth-yl}-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxyl-ate. |
| title_full | Penta-fluoro-phenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azido-methyl-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxamido]-meth-yl}-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxyl-ate. |
| title_fullStr | Penta-fluoro-phenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azido-methyl-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxamido]-meth-yl}-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxyl-ate. |
| title_full_unstemmed | Penta-fluoro-phenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azido-methyl-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxamido]-meth-yl}-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxyl-ate. |
| title_short | Penta-fluoro-phenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azido-methyl-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxamido]-meth-yl}-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxyl-ate. |
| title_sort | penta fluoro phenyl 3r 4r 5s 5 3r 4r 5s 5 azido methyl 3 4 dimeth oxy 2 3 4 5 tetra hydro furan 3 carboxamido meth yl 3 4 dimeth oxy 2 3 4 5 tetra hydro furan 3 carboxyl ate |
| work_keys_str_mv | AT simonem pentafluorophenyl3r4r5s53r4r5s5azidomethyl34dimethoxy2345tetrahydrofuran3carboxamidomethyl34dimethoxy2345tetrahydrofuran3carboxylate AT edwardsa pentafluorophenyl3r4r5s53r4r5s5azidomethyl34dimethoxy2345tetrahydrofuran3carboxamidomethyl34dimethoxy2345tetrahydrofuran3carboxylate AT parkers pentafluorophenyl3r4r5s53r4r5s5azidomethyl34dimethoxy2345tetrahydrofuran3carboxamidomethyl34dimethoxy2345tetrahydrofuran3carboxylate AT tranterg pentafluorophenyl3r4r5s53r4r5s5azidomethyl34dimethoxy2345tetrahydrofuran3carboxamidomethyl34dimethoxy2345tetrahydrofuran3carboxylate AT fleetg pentafluorophenyl3r4r5s53r4r5s5azidomethyl34dimethoxy2345tetrahydrofuran3carboxamidomethyl34dimethoxy2345tetrahydrofuran3carboxylate AT watkind pentafluorophenyl3r4r5s53r4r5s5azidomethyl34dimethoxy2345tetrahydrofuran3carboxamidomethyl34dimethoxy2345tetrahydrofuran3carboxylate |