Advances in the Synthesis of Homochiral (-)-1-Azafagomine and (+)-5-epi-1-Azafagomine. 1-N-Phenyl Carboxamide Derivatives of both Enantiomers of 1-Azafagomine: Leads for the Synthesis of Active α-Glycosidase Inhibitors.
M. José Alves; Flora T. Costa; Vera C. M. Duarte; Antonio Gil Fortes; José A. Martins; Nuno M. Micaelo; Journal of Organic Chemistry 76 (2011) 9584–9592; doi:10.1021/jo201486q

data_4026757
_publ_section_title
;
 Advances in the Synthesis of Homochiral (-)-1-Azafagomine and
 (+)-5-epi-1-Azafagomine. 1-N-Phenyl Carboxamide Derivatives of both
 Enantiomers of 1-Azafagomine: Leads for the Synthesis of Active
 \a-Glycosidase Inhibitors.
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9584
_journal_page_last               9592
_journal_paper_doi               10.1021/jo201486q
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C29 H33 N3 O14'
_chemical_formula_sum            'C29 H33 N3 O14'
_chemical_formula_weight         647.58
_chemical_name_common            VCD-68
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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_date             2011-01-20T13:30:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 101.924(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.263(3)
_cell_length_b                   7.0712(13)
_cell_length_c                   29.628(5)
_cell_measurement_reflns_used    3517
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.15
_cell_measurement_wavelength     0.71073
_cell_volume                     3128.7(10)
_computing_cell_refinement       'APEX2 v2010.11-3 (Bruker AXS, 2010)'
_computing_data_collection       'APEX2 v2010.11-3 (Bruker AXS, 2010)'
_computing_data_reduction        'APEX2 v2010.11-3 (Bruker AXS, 2010)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       '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  0.0650
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            25307
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.7792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER AXS - SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       needle
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1086
_refine_ls_number_reflns         6908
_refine_ls_number_restraints     1660
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0603P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.097
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                5112
_reflns_number_total             6908
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo201486q_si_002.cif
_cod_data_source_block           um02agf1n
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4026757