Total Synthesis of Ezetimibe, a Cholesterol Absorption Inhibitor
Marcin Śnieżek; Sebastian Stecko; Irma Panfil; Bartłomiej Furman; Marek Chmielewski; Journal of Organic Chemistry 78 (2013) 7048–7057; doi:10.1021/jo400807c

data_4028414
_publ_section_title
;
 Total Synthesis of Ezetimibe, a Cholesterol Absorption Inhibitor
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7048
_journal_page_last               7057
_journal_paper_doi               10.1021/jo400807c
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_formula_sum            'C31 H25 F2 N O4'
_chemical_formula_weight         513.52
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.709(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7715(5)
_cell_length_b                   9.7199(5)
_cell_length_c                   12.6088(7)
_cell_measurement_reflns_used    1054
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      53.70
_cell_measurement_theta_min      3.62
_cell_volume                     1276.85(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_sigmaI/netI    0.1066
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6266
_diffrn_reflns_theta_full        67.43
_diffrn_reflns_theta_max         67.43
_diffrn_reflns_theta_min         5.82
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  0.9397
_exptl_absorpt_correction_T_min  0.7391
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(4)
_refine_ls_extinction_coef       0.0055(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.245
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         3671
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.245
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0699
_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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1645
_refine_ls_wR_factor_ref         0.1896
_reflns_number_gt                2358
_reflns_number_total             3671
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400807c_si_004.cif
_cod_data_source_block           msa221_b_0m
_cod_original_cell_volume        1276.85(11)
_cod_database_code               4028414