A Method for the Preparation of Differentiatedtrans-1,2-Diol Derivatives with Enantio- and Diastereocontrol
Sang Min Lim; Nicholas Hill; Andrew G. Myers; Journal of the American Chemical Society 131 (2009) 5763–5765; doi:10.1021/ja901283q

data_4104255
_publ_section_title
;
 A Method for the Preparation of Differentiatedtrans-1,2-Diol Derivatives
 with Enantio- and Diastereocontrol
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5763
_journal_page_last               5765
_journal_paper_doi               10.1021/ja901283q
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_compound_source        'chemical synthesis'
_chemical_formula_iupac          'C32 H46 Br2 O6 Si2'
_chemical_formula_moiety         'C32 H46 Br2 O6 Si2'
_chemical_formula_structural     'C32 H46 Br2 O6 Si2'
_chemical_formula_sum            'C32 H46 Br2 O6 Si2'
_chemical_formula_weight         742.69
_chemical_name_common            B259
_chemical_name_systematic
; 
(1R,3R,4R,6R)-4,6-Bis(tert-butyldimethylsilyloxy)cyclohexane-1,3-diyl
Bis(4-bromobenzoate)
;
_space_group_IT_number           4
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.972(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.4443(3)
_cell_length_b                   20.6728(9)
_cell_length_c                   12.0342(5)
_cell_measurement_reflns_used    18928
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.80
_cell_measurement_theta_min      2.60
_cell_volume                     1847.55(13)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction
;
SAINT V7.34A (Bruker AXS, 2006b), SADABS (Bruker AXS, 2004)
;
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_solution    'SHELXTL v6.12 (Bruker AXS, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       '\w scans, 3065 0.5\% rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            51031
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.296
_exptl_absorpt_correction_T_max  0.78709
_exptl_absorpt_correction_T_min  0.54681
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2004)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.009(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         8478
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0281P)^2^+0.2560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0718
_reflns_number_gt                7521
_reflns_number_total             8478
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja901283q_si_002.cif
_cod_data_source_block           agm068
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4104255