Synthesis of Postulated Molecular Probes: Stereoselective Free-Radical-MediatedC-Glycosylation in Tandem with Hydrogen Transfer
Yvan Guindon; Mohammed Bencheqroun; Abderrahim Bouzide; Journal of the American Chemical Society 127 (2005) 554–558; doi:10.1021/ja046389y

data_4111396
_publ_contact_author
;
    Dr Yvan Guindon
    Institut de recherches cliniques de Montr\'eal
    110 ouest, Avenue des Pins
    Montr\'eal, Qu\'ebec
    Canada H2W 1R7
;
_publ_contact_author_email       guindoy@ircm.umontreal.ca
_publ_contact_author_fax         '514 987 5789'
_publ_contact_author_phone       '514 987 5786'
_publ_section_title
;
 Synthesis of Postulated Molecular Probes: Stereoselective
 Free-Radical-MediatedC-Glycosylation in Tandem with Hydrogen Transfer
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              554
_journal_page_last               558
_journal_paper_doi               10.1021/ja046389y
_journal_volume                  127
_journal_year                    2005
_chemical_compound_source        'synthesized by the authors, see text'
_chemical_formula_moiety         'C33 H46 O21'
_chemical_formula_sum            'C33 H46 O21'
_chemical_formula_weight         778.698
_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           'SHELXL96 (Sheldrick, 1996)'
_cell_angle_alpha                90.00
_cell_angle_beta                 98.67(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.841(3)
_cell_length_b                   17.598(6)
_cell_length_c                   12.876(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      15.00
_cell_volume                     1980.4(12)
_computing_cell_refinement       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction        'NRC-2, NRC-2A (Ahmed et al, 1973)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXL96 (Sheldrick, 1996)'
_computing_structure_refinement  'SHELXL96 (Sheldrick, 1996)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus xray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54056
_diffrn_reflns_av_R_equivalents  0.080
_diffrn_reflns_av_sigmaI/netI    0.0768
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37308
_diffrn_reflns_theta_max         69.83
_diffrn_reflns_theta_min         3.47
_diffrn_standards_decay_%        'no decay, variation  3.6'
_diffrn_standards_interval_time  60
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.947
_exptl_absorpt_correction_T_max  0.9357
_exptl_absorpt_correction_T_min  0.7951
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'ABSORP in NRCVAX (Gabe et al, 1989)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.3059
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             824.0
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.0052(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL96 (Sheldrick, 1996)'
_refine_ls_goodness_of_fit_all   0.766
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         7519
_refine_ls_number_restraints     712
_refine_ls_restrained_S_all      0.864
_refine_ls_restrained_S_obs      1.288
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0441P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1098
_refine_ls_wR_factor_ref         0.0954
_reflns_number_gt                3491
_reflns_number_total             7519
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja046389ysi20040701_113617.cif
_cod_data_source_block           guin15
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4111396