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_4032446
_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 H51 N O3'
_chemical_formula_weight         569.79
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2203(2)
_cell_length_b                   12.1227(4)
_cell_length_c                   37.8288(13)
_cell_measurement_reflns_used    7090
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      63.143
_cell_measurement_theta_min      2.336
_cell_volume                     3311.14(18)
_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 0.790
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_device_type  'Bruker X8-apex'
_diffrn_measurement_method       strategy
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.790
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            7090
_diffrn_reflns_point_group_measured_fraction_full 0.765
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         63.143
_diffrn_reflns_theta_min         2.336
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_T_min  0.836
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1766 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.22(11)
_refine_ls_extinction_coef       0.0019(4)
_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   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0691P)^2^+0.4391P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1144
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.732
_reflns_Friedel_fraction_max     0.822
_reflns_number_gt                4424
_reflns_number_total             4596
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00438_si_001.cif
_cod_data_source_block           p212121
_cod_depositor_comments
'Adding full bibliography for 4032445--4032446.cif.'
_cod_database_code               4032446
_shelx_estimated_absorpt_t_min   0.836
_shelx_estimated_absorpt_t_max   0.922
_shelxl_version_number           2013-4
_shelx_res_checksum              8605
_shelx_hkl_checksum              13735