Total Synthesis and Biological Evaluation of 19-Hydroxysarmentogenin-3 -O-α-l-rhamnoside, Trewianin, and Their Aglycons.
Urabe, Daisuke; Nakagawa, Yuki; Mukai, Ken; Fukushima, Kei-Ichiro; Aoki, Naoto; Itoh, Hiroaki; Nagatomo, Masanori; Inoue, Masayuki; The Journal of organic chemistry 83 (2018) 13888–13910; doi:10.1021/acs.joc.8b02219

data_4034875
_publ_section_title
;
 Total Synthesis and Biological Evaluation of 19-Hydroxysarmentogenin-3
 -O-\a-l-rhamnoside, Trewianin, and Their Aglycons.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13888
_journal_page_last               13910
_journal_paper_doi               10.1021/acs.joc.8b02219
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H40 O5 Si'
_chemical_formula_sum            'C26 H40 O5 Si'
_chemical_formula_weight         460.68
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.862(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.7367(3)
_cell_length_b                   22.9731(7)
_cell_length_c                   16.5877(12)
_cell_measurement_reflns_used    5308
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.17
_cell_measurement_theta_min      3.29
_cell_volume                     2566.9(2)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, 2006)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku VariMax with RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30321
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.069
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1000.00
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.250
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  4070 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     580
_refine_ls_number_reflns         8872
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0502P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                7396
_reflns_number_total             8872
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo8b02219_si_003.cif
_cod_data_source_block           sc0890
_cod_original_cell_volume        2566.9(3)
_cod_database_code               4034875