Asymmetric Total Synthesis of (+)-(2R,4’R,8’R)--Tocopherol Enabled by Enzymatic Desymmetrization
Yang, Haidi; Liu, Jinyao; Hu, Pan; Gao, Liang; Huang, Zedu; Chen, Fen-Er; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00384H

data_7158575
_publ_section_title
;
 Asymmetric Total Synthesis of
 (+)-(2R,4&#x2019;R,8&#x2019;R)-&#xF061;-Tocopherol Enabled by Enzymatic
 Desymmetrization
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00384H
_journal_year                    2022
_chemical_formula_sum            'C14 H20 O3'
_chemical_formula_weight         236.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-10-12 deposited with the CCDC.	2022-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.5260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   38.9060(12)
_cell_length_b                   5.7838(2)
_cell_length_c                   11.1782(3)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      59.43
_cell_measurement_theta_min      3.52
_cell_volume                     2455.50(13)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16142
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         58.993
_diffrn_reflns_theta_min         3.664
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_correction_T_min  0.579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       sheet
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
; 
 Flack x determined using 2036 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.14(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5341
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0751P)^2^+0.5608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1270
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                4979
_reflns_number_total             5341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00384h2.cif
_cod_data_source_block           ga_210601b_b
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7158575
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.829
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              61258