Synthesis of HIV-Maturation Inhibitor BMS-955176 from Betulin by an Enabling Oxidation Strategy.
Ortiz, Adrian; Soumeillant, Maxime; Savage, Scott A.; Strotman, Neil A.; Haley, Matthew; Benkovics, Tamas; Nye, Jeffrey; Xu, Zhongmin; Tan, Yichen; Ayers, Sloan; Gao, Qi; Kiau, Susanne; The Journal of organic chemistry 82 (2017) 4958–4963; doi:10.1021/acs.joc.7b00438

data_4032445
_publ_section_title
;
 Synthesis of HIV-Maturation Inhibitor BMS-955176 from Betulin by an
 Enabling Oxidation Strategy.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4958
_journal_page_last               4963
_journal_paper_doi               10.1021/acs.joc.7b00438
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C38 H53 N O4'
_chemical_formula_weight         587.81
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.9331(2)
_cell_length_b                   10.9331(2)
_cell_length_c                   54.6630(10)
_cell_measurement_reflns_used    53542
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      60.568
_cell_measurement_theta_min      4.123
_cell_volume                     6534.0(2)
_computing_cell_refinement       APEX2
_computing_data_collection       APEX2
_computing_data_reduction        APEX2
_computing_molecular_graphics    Mercury
_computing_publication_material  Mercury
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    APEX2
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0.9
_diffrn_measured_fraction_theta_full 0.833
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Apex'
_diffrn_measurement_method       strategy
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_Laue_measured_fraction_full 0.833
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -61
_diffrn_reflns_number            53542
_diffrn_reflns_point_group_measured_fraction_full 0.824
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         60.568
_diffrn_reflns_theta_min         4.123
_diffrn_source                   'rotating anode micro-source'
_exptl_absorpt_coefficient_mu    0.593
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2560
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.141
_refine_ls_abs_structure_details
;
 Flack x determined using 1921 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       0.0040(3)
_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   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         4882
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0626P)^2^+0.7963P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0953
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_full    0.811
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                4863
_reflns_number_total             4882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00438_si_002.cif
_cod_data_source_block           p43212
_cod_depositor_comments
'Adding full bibliography for 4032445--4032446.cif.'
_cod_original_cell_volume        6534.0(3)
_cod_database_code               4032445
_shelx_estimated_absorpt_t_min   0.891
_shelx_estimated_absorpt_t_max   0.922
_shelxl_version_number           2013-4
_shelx_res_checksum              52339
_shelx_hkl_checksum              90607