Unexpected Anomeric Selectivity of a 1-C-Arylglycal Donor in Kdo Glycoside Synthesis
Yuxin Qian; Jianhao Feng; Masood Parvez; Chang-Chun Ling; Journal of Organic Chemistry 77 (2012) 96–107; doi:10.1021/jo201531j

data_4026823
_publ_contact_author
;
    Masood Parvez
    Department of Chemistry
    University of Calgary
    2500 University Drive N.W.
    Calgary, Alberta, Canada T2N 1N4  
;
_publ_contact_author_email       ' parvez@ucalgary.ca '
_publ_contact_author_fax         ' (403)289-9488 '
_publ_contact_author_phone       ' (403)220-5348 '
_publ_section_title
;
 Unexpected Anomeric Selectivity of a 1-C-Arylglycal Donor in Kdo
 Glycoside Synthesis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              96
_journal_page_last               107
_journal_paper_doi               10.1021/jo201531j
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H27 I O6'
_chemical_formula_sum            'C20 H27 I O6'
_chemical_formula_weight         490.32
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.8944(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6964(3)
_cell_length_b                   10.2021(3)
_cell_length_c                   16.7996(3)
_cell_measurement_reflns_used    4917
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2143.68(9)
_computing_cell_refinement       'APEX2 '
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 & PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius APEX2 CCD'
_diffrn_measurement_method       ' \w and \f scans '
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7657
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.23
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.525
_exptl_absorpt_correction_T_max  0.8877
_exptl_absorpt_correction_T_min  0.7925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1997)'
_exptl_crystal_colour            Colorless'
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_description       Prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack (1983); using 2597 Friedel pairs'
_refine_ls_abs_structure_Flack   0.030(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         7657
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0211P)^2^+2.9193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0666
_reflns_number_gt                7355
_reflns_number_total             7657
_reflns_threshold_expression     '(I) > 2.0 \s(I)'
_cod_data_source_file            jo201531j_si_003.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4026823