Synthesis and Evaluation of Eight- and Four-Membered Iminosugar Analogues as Inhibitors of Testicular Ceramide-Specific Glucosyltransferase, Testicular β-Glucosidase 2, and Other Glycosidases
Jae Chul Lee; Subhashree Francis; Dinah Dutta; Vijayalaxmi Gupta; Yan Yang; Jin-Yi Zhu; Joseph S. Tash; Ernst Schönbrunn; Gunda I. Georg; Journal of Organic Chemistry 77 (2012) 3082–3098; doi:10.1021/jo202054g

data_4027093
_publ_section_title
;
 Synthesis and Evaluation of Eight- and Four-Membered Iminosugar Analogues
 as Inhibitors of Testicular Ceramide-Specific Glucosyltransferase,
 Testicular \b-Glucosidase 2, and Other Glycosidases
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3082
_journal_page_last               3098
_journal_paper_doi               10.1021/jo202054g
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration rm
_chemical_formula_moiety         '2(C16 H33 N O5), H2 O'
_chemical_formula_sum            'C32 H68 N2 O11'
_chemical_formula_weight         656.88
_chemical_name_common            08001
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.751(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.3632(13)
_cell_length_b                   8.1773(10)
_cell_length_c                   21.547(3)
_cell_measurement_reflns_used    2524
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.82
_cell_measurement_theta_min      2.66
_cell_volume                     1825.1(4)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART Platform CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_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  0.0746
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13985
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         0.95
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.9697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_description       plate
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details
'Flack H D (1983), 2945 Friedel Pairs, Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0917P)^2^+1.2808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1700
_reflns_number_gt                2408
_reflns_number_total             3487
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202054g_si_002.cif
_cod_data_source_block           08001
_cod_database_code               4027093