Stereoselective synthesis of 2,2-bis(C-branched-chain)glucopyranosid-3-ulose via an autoxidation‒Michael addition reaction
Liu, Hong-Min; Zhang, Fuyi; Zou, Da-Peng; Chemical Communications (Cambridge, United Kingdom)  (2003) 2044–2045; doi:10.1039/b306227a

data_7113576
_publ_section_title
;
 Stereoselective synthesis of 2,2-bis(C-branched-chain)glucopyranosid-3-ulose
 via an autoxidation--Michael addition reaction
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   16
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2044
_journal_page_last               2045
_journal_paper_doi               10.1039/b306227a
_journal_year                    2003
_chemical_formula_sum            'C21 H22 O8'
_chemical_formula_weight         402.39
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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                 103.36(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.8818(18)
_cell_length_b                   8.5242(17)
_cell_length_c                   13.488(3)
_cell_measurement_reflns_used    210
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      25.2
_cell_measurement_theta_min      2
_cell_volume                     993.5(4)
_computing_cell_refinement       raxis
_computing_data_collection       raxis
_computing_data_reduction        raxis
_computing_molecular_graphics    texsan
_computing_publication_material  texsan
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.892
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  R-axis-IV
_diffrn_measurement_method       'Osillation  frames'
_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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2783
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_correction_T_min  0.9696
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.6(16)
_refine_ls_extinction_coef       0.022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2686
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0645P)^2^+0.0886P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                2378
_reflns_number_total             2686
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7103853
_cod_data_source_file            b306227a.txt
_cod_data_source_block           compound_3
_cod_original_cell_volume        993.6(3)
_cod_original_sg_symbol_H-M      p2(1)
_cod_database_code               7113576