Facile, Efficient, and Enantiospecific Syntheses of 1,1'-N-Linked Pseudodisaccharides as a New Class of Glycosidase Inhibitors
Tony K. M. Shing; Connie S. K. Kwong; Aries W. C. Cheung; Stanton H.-L. Kok; Zhifeng Yu; Jianmei Li; Christopher H. K. Cheng; Journal of the American Chemical Society 126 (2004) 15990–15992; doi:10.1021/ja0470158

data_4113255
_publ_section_title
;
 Facile, Efficient, and Enantiospecific Syntheses of 1,1'-N-Linked
 Pseudodisaccharides as a New Class of Glycosidase Inhibitors
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15990
_journal_page_last               15992
_journal_paper_doi               10.1021/ja0470158
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C13 H22 O6'
_chemical_formula_weight         274.31
_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                   6.9969(4)
_cell_length_b                   11.1153(6)
_cell_length_c                   18.5163(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1440.06(14)
_computing_cell_refinement       'BRUKER SMART CCD DIFFRACTOMETER'
_computing_data_collection       'BRUKER SMART CCD DIFFRACTOMETER'
_computing_data_reduction        'BRUKER SMART CCD DIFFRACTOMETER'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER SMART CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA SCAN'
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6647
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_correction_T_min  0.8815
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            BLOCK
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             592
_exptl_crystal_size_max          1.30
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.354
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+0.0138P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0886
_reflns_number_gt                1874
_reflns_number_total             2066
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0470158si20040520_095607.cif
_cod_data_source_block           ast4b
_cod_database_code               4113255