Synthesis of 6-Alkyluridines from 6-Cyanouridine via Zinc(II) Chloride-Catalyzed Nucleophilic Substitution with Alkyl Grignard Reagents
Yu-Chiao Shih; Ya-Ying Yang; Chun-Chi Lin; Tun-Cheng Chien; Journal of Organic Chemistry 78 (2013) 4027–4036; doi:10.1021/jo400364p

data_4028172
_publ_section_title
;
 Synthesis of 6-Alkyluridines from 6-Cyanouridine via Zinc(II)
 Chloride-Catalyzed Nucleophilic Substitution with Alkyl Grignard Reagents
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4027
_journal_page_last               4036
_journal_paper_doi               10.1021/jo400364p
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C8 H9 N3 O'
_chemical_formula_sum            'C8 H9 N3 O'
_chemical_formula_weight         163.18
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_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.749(2)
_cell_angle_beta                 76.821(2)
_cell_angle_gamma                83.472(3)
_cell_formula_units_Z            2
_cell_length_a                   6.7751(13)
_cell_length_b                   7.1451(13)
_cell_length_c                   8.7889(16)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     402.38(13)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1282
_diffrn_reflns_av_sigmaI/netI    0.0879
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2551
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_correction_T_min  0.9572
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       prism
_exptl_crystal_F_000             172
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.248
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.248
_refine_ls_R_factor_all          0.1242
_refine_ls_R_factor_gt           0.1088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3069
_refine_ls_wR_factor_ref         0.3292
_reflns_number_gt                1016
_reflns_number_total             1365
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400364p_si_002.cif
_cod_data_source_block           a10953
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