Diastereoselective addition of sugar radicals to camphorsultam glyoxilic oxime ether: a route toward C-glycosylthreonine and allothreonine
Bragnier, Nicolas; Guillot, Regis; Scherrmann, Marie-Christine; Organic & Biomolecular Chemistry 7 (2009) 3918–3921; doi:10.1039/b910050d

data_7150732
_publ_section_title
;
 Diastereoselective addition of sugar radicals to camphorsultam
 glyoxilic oxime ether: a route toward C-glycosylthreonine and
 allothreonine
;
_journal_issue                   19
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              3918
_journal_page_last               3921
_journal_paper_doi               10.1039/b910050d
_journal_volume                  7
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H26 O11'
_chemical_formula_sum            'C18 H26 O11'
_chemical_formula_weight         418.39
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9034(12)
_cell_length_b                   10.2924(13)
_cell_length_c                   20.413(2)
_cell_measurement_reflns_used    7468
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      33.41
_cell_measurement_theta_min      2.22
_cell_volume                     2080.7(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22090
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         37.38
_diffrn_reflns_theta_min         2.00
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         9135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0753P)^2^+0.1827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                6941
_reflns_number_total             9135
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b910050d.txt
_cod_data_source_block           528GuillotICMMO
_cod_database_code               7150732