Synthesis of Aryl C-Glycosides via Iron-Catalyzed Cross Coupling of Halosugars: Stereoselective Anomeric Arylation of Glycosyl Radicals.
Adak, Laksmikanta; Kawamura, Shintaro; Toma, Gabriel; Takenaka, Toshio; Isozaki, Katsuhiro; Takaya, Hikaru; Orita, Akihiro; Li, Ho C.; Shing, Tony K. M.; Nakamura, Masaharu; Journal of the American Chemical Society 139 (2017) 10693–10701; doi:10.1021/jacs.7b03867

data_4131304
_publ_section_title
;
 Synthesis of Aryl C-Glycosides via Iron-Catalyzed Cross Coupling of
 Halosugars: Stereoselective Anomeric Arylation of Glycosyl Radicals.
;
_journal_issue                   31
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10693
_journal_page_last               10701
_journal_paper_doi               10.1021/jacs.7b03867
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C17 H21 O7'
_chemical_formula_sum            'C17 H21 O7'
_chemical_formula_weight         337.35
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      92
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   11.8330(15)
_cell_length_b                   11.8330(15)
_cell_length_c                   24.665(4)
_cell_measurement_reflns_used    11595
_cell_measurement_temperature    113
_cell_measurement_theta_max      31.36
_cell_measurement_theta_min      1.91
_cell_volume                     3453.6(8)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      113
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            55016
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1432.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.170
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3910
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0747P)^2^+0.1871P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                3754
_reflns_number_total             3910
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja7b03867_si_004.cif
_cod_data_source_block           LA_Ph_01
_cod_original_cell_volume        3453.5(8)
_cod_database_code               4131304