Large-Scale Synthesis of All Stereoisomers of a 2,3-Unsaturated C-Glycoside Scaffold
Baudouin Gerard; Jean-Charles Marié; Bhaumik A. Pandya; Maurice D. Lee IV; Haibo Liu; Lisa A. Marcaurelle; Journal of Organic Chemistry 76 (2011) 1898–1901; doi:10.1021/jo1022926

data_4026111
_publ_section_title
;
 Large-Scale Synthesis of All Stereoisomers of a 2,3-Unsaturated
 C-Glycoside Scaffold
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1898
_journal_page_last               1901
_journal_paper_doi               10.1021/jo1022926
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C33 H35 N O6 Si'
_chemical_formula_weight         569.71
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 92.6080(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.2912(4)
_cell_length_b                   10.6350(2)
_cell_length_c                   15.6481(3)
_cell_measurement_reflns_used    9343
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.33
_cell_measurement_theta_min      4.81
_cell_volume                     3040.82(11)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 v2009.3.0 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33183
_diffrn_reflns_theta_full        68.84
_diffrn_reflns_theta_max         68.84
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    1.047
_exptl_absorpt_correction_T_max  0.8180
_exptl_absorpt_correction_T_min  0.6280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       plate
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.053(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5395
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0246
_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^)+(0.0403P)^2^+1.0117P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0654
_reflns_number_gt                5382
_reflns_number_total             5395
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1022926_si_003.cif
_cod_data_source_block           d09061
_cod_database_code               4026111