A New Method for the Stereoselective Synthesis of α- and β-Glycosylamines Using the Burgess Reagent
K. C. Nicolaou; Scott A. Snyder; Annie Z. Nalbandian; Deborah A. Longbottom; Journal of the American Chemical Society 126 (2004) 6234–6235; doi:10.1021/ja049293c

data_4112593
_publ_section_title
;
 A New Method for the Stereoselective Synthesis of \a- and
 \b-Glycosylamines Using the Burgess Reagent
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6234
_journal_page_last               6235
_journal_paper_doi               10.1021/ja049293c
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C12 H23 N O7'
_chemical_formula_weight         293.31
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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                   5.0446(8)
_cell_length_b                   9.8623(16)
_cell_length_c                   31.428(5)
_cell_measurement_reflns_used    3421
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.0
_cell_measurement_theta_min      2.5
_cell_volume                     1563.6(4)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            14118
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.44
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_type   Semi-empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       Plate-like
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0635P)^2^+0.0413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1377
_reflns_number_gt                2087
_reflns_number_total             3612
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja049293csi20040209_015757.cif
_cod_data_source_block           ss2p
_cod_database_code               4112593