A highly diastereoselective “super silyl” governed aldol reaction: synthesis of α,β-dioxyaldehydes and 1,2,3-triols
Gati, Wafa; Yamamoto, Hisashi; Chem. Sci. 7 (2016) 394–; doi:10.1039/C5SC03307A

data_1534349
_publ_section_title
;
 A highly diastereoselective &#x201C;super silyl&#x201D; governed aldol
 reaction: synthesis of \a,\b-dioxyaldehydes and 1,2,3-triols
;
_journal_issue                   1
_journal_name_full               'Chem. Sci.'
_journal_page_first              394
_journal_paper_doi               10.1039/C5SC03307A
_journal_volume                  7
_journal_year                    2016
_chemical_formula_moiety         'C30 H54 O3 Si4'
_chemical_formula_sum            'C30 H54 O3 Si4'
_chemical_formula_weight         575.10
_chemical_name_common            1,2,3-triol
_chemical_name_systematic
(3R,4S,5S)-4-benzyloxy-2,2-dimethyl-5-tris(trimethylsilyl)siloxy-6-phenylhex-1-en-3-ol
_chemical_properties_physical    'Moisture-sensitive, Oxygen-sensitive'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2015-06-30 deposited with the CCDC.
2015-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.084(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   11.113(3)
_cell_length_b                   35.197(9)
_cell_length_c                   9.482(3)
_cell_measurement_reflns_used    9282
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.98
_cell_volume                     3626.6(18)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.910
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1530
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20638
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1884.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.340
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     334
_refine_ls_number_reflns         7577
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0847
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0780P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2172
_reflns_number_gt                2990
_reflns_number_total             7577
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c5sc03307a2.cif
_cod_data_source_block           User-defined
_cod_depositor_comments
;
Adding full bibliography for 1534349--1534350.cif.

2019-03-17
Fixing wrong Z value.                 miguel
;
_cod_original_cell_volume        3626.5(16)
_cod_original_formula_units_Z    6
_cod_database_code               1534349