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_1534350
_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         'C24 H64 O3 Si8'
_chemical_formula_sum            'C24 H64 O3 Si8'
_chemical_formula_weight         625.45
_chemical_name_common            'bissilyloxy aldehyde'
_chemical_name_systematic
'(2R,3R)-2,3-bis(tris(trimethylsilyl)siloxy)-hexanal '
_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                 105.69(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   16.614(19)
_cell_length_b                   18.221(19)
_cell_length_c                   14.051(16)
_cell_measurement_reflns_used    5092
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      5.90
_cell_volume                     4095(8)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15'
_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      173
_diffrn_detector_area_resol_mean 6.827
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.2671
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            41388
_diffrn_reflns_theta_full        27.76
_diffrn_reflns_theta_max         27.77
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.014
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1376.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         1.610
_refine_diff_density_min         -0.500
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.285
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     306
_refine_ls_number_reflns         9468
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.2228
_refine_ls_shift/su_max          0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.5310
_reflns_number_gt                3829
_reflns_number_total             9468
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c5sc03307a2.cif
_cod_data_source_block           wafa
_cod_depositor_comments
'Adding full bibliography for 1534349--1534350.cif.'
_cod_database_code               1534350