Total Synthesis of 1α,25-Dihydroxyvitamin D3 (Calcitriol) Through a Si-Assisted Allylic Substitution
López-Pérez, Borja; Maestro, Miguel A.; Mouriño, Antonio; Chem. Commun.  (2017) –; doi:10.1039/C7CC04690A

data_7120350
_publ_section_title
;
 Total Synthesis of 1\a,25-Dihydroxyvitamin D3 (Calcitriol) Through a
 Si-Assisted Allylic Substitution
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC04690A
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H22 O4 S'
_chemical_formula_sum            'C17 H22 O4 S'
_chemical_formula_weight         322.41
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-02-24 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4726(4)
_cell_length_b                   13.7659(8)
_cell_length_c                   15.3749(9)
_cell_measurement_reflns_used    1953
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.245
_cell_measurement_theta_min      3.035
_cell_volume                     1581.57(16)
_computing_cell_refinement
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_data_reduction
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            114970
_diffrn_reflns_theta_full        36.36
_diffrn_reflns_theta_max         36.36
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.9573
_exptl_absorpt_correction_T_min  0.8884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         7697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.1207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0688
_reflns_number_gt                7325
_reflns_number_total             7697
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc04690a2.cif
_cod_data_source_block           anc1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7120350