Protecting-Group-Mediated Diastereoselective Synthesis of C4'-Methylated Uridine Analogs and their Activity against the Human Respiratory Syncytial Virus.
Köllmann, Christoph; Sake, Svenja M.; Jones, Peter G.; Pietschmann, Thomas; Werz, Daniel B.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03425

data_4037962
_publ_section_title
;
 Protecting-Group-Mediated Diastereoselective Synthesis of C4'-Methylated
 Uridine Analogs and their Activity against the Human Respiratory
 Syncytial Virus.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03425
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H20 N2 O6'
_chemical_formula_weight         408.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 92.4786(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.99677(7)
_cell_length_b                   7.61343(8)
_cell_length_c                   20.4686(2)
_cell_measurement_reflns_used    42415
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.6420
_cell_measurement_theta_min      2.2350
_cell_volume                     933.640(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-2017
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyP'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            58257
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        75.000
_diffrn_reflns_theta_max         78.029
_diffrn_reflns_theta_min         4.324
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1790 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3967
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+0.2145P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0882
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3936
_reflns_number_total             3967
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03425_si_004.cif
_cod_data_source_block           koell5
_cod_original_cell_volume        933.641(17)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4037962
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.878
_shelx_estimated_absorpt_t_max   0.965
_shelx_res_checksum              31596
_shelx_hkl_checksum              90462