Convergent Approach toward the Synthesis of the Stereoisomers of C-6 Homologues of 1-Deoxynojirimycin and Their Analogues: Evaluation as Specific Glycosidase Inhibitors
Ganesh Pandey; Shrinivas G. Dumbre; M. Islam Khan; M. Shabab; Journal of Organic Chemistry 71 (2006) 8481–8488; doi:10.1021/jo061455v

data_4022045
_publ_section_title
;
 Convergent Approach toward the Synthesis of the Stereoisomers
 of C-6 Homologues of 1-Deoxynojirimycin and Their Analogues:
 Evaluation as Specific Glycosidase Inhibitors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8481
_journal_page_last               8488
_journal_paper_doi               10.1021/jo061455v
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C18 H25 N O4'
_chemical_formula_sum            'C18 H25 N O4'
_chemical_formula_weight         319.39
_chemical_melting_point          358.6(15)
_chemical_name_common            Azasugar
_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                 92.897(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.3217(7)
_cell_length_b                   9.7758(13)
_cell_length_c                   16.549(2)
_cell_measurement_reflns_used    995
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.069
_cell_measurement_theta_min      2.42
_cell_volume                     859.8(2)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    'SHELXTL and PLATON'
_computing_publication_material  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 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_device_type  'CCD Area Detector'
_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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4783
_diffrn_reflns_theta_full        23.35
_diffrn_reflns_theta_max         23.35
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_correction_T_min  0.9637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2373
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0724
_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^)+(0.1240P)^2^+0.5104P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2217
_refine_ls_wR_factor_ref         0.2235
_reflns_number_gt                2244
_reflns_number_total             2373
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061455vsi20060718_051303_2.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'multiscan' changed to 'multi-scan'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '84-87 degree centigrade' was changed
to '358.6(15)' - it was converted from degrees Celsius(C) to
Kelvins(K), the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022045