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_4028413
_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 O3'
_chemical_formula_weight         497.52
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8450(2)
_cell_length_b                   11.3855(3)
_cell_length_c                   27.6202(7)
_cell_measurement_reflns_used    3150
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      58.35
_cell_measurement_theta_min      3.20
_cell_volume                     2467.02(11)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            17163
_diffrn_reflns_theta_full        68.80
_diffrn_reflns_theta_max         68.80
_diffrn_reflns_theta_min         3.20
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8467
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.09(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0454P)^2^+0.1723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0944
_reflns_number_gt                3852
_reflns_number_total             4531
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400807c_si_003.cif
_cod_data_source_block           msa_167_b_0m
_cod_database_code               4028413