Ugi three-component coupling strategy for the synthesis of bridged bicyclic iminosugars.
Rakesh, Goparaju; Vinaykumar, Allam; Soniya, Dommati; Sridhar, B.; Subba Reddy, B. V.; Organic & biomolecular chemistry 23 (2025) 10311–10314; doi:10.1039/d5ob01246e

data_7160803
_publ_section_title
;
 Ugi three-component coupling strategy for the synthesis of bridged
 bicyclic iminosugars.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10311
_journal_page_last               10314
_journal_paper_doi               10.1039/d5ob01246e
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H34 N2 O3'
_chemical_formula_sum            'C20 H34 N2 O3'
_chemical_formula_weight         350.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-07-16 deposited with the CCDC.	2025-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.269(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2400(15)
_cell_length_b                   9.810(2)
_cell_length_c                   17.335(4)
_cell_measurement_reflns_used    6171
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23.0295
_cell_measurement_theta_min      2.3535
_cell_volume                     1059.4(4)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2019)'
_computing_data_collection       '<i>APEX5</i> (Bruker, 2023)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2019)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 7.391
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III C14'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14116
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.463
_diffrn_reflns_theta_min         2.354
_diffrn_source                   'Incoatec I\mS 3.0'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 1356 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4313
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0492P)^2^+0.0595P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                3441
_reflns_number_total             4313
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01246e2.cif
_cod_data_source_block           mo_VA145_0m_a
_cod_depositor_comments          'Adding full bibliography for 7160803.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7160803
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              18668