Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase.
Oliveira Udry, Guillermo A.; Repetto, Evangelina; Vega, Daniel R.; Varela, Oscar; The Journal of organic chemistry 81 (2016) 4179–4189; doi:10.1021/acs.joc.6b00514

data_4031998
_publ_section_title
;
 Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar
 Cycloadducts. Evaluation as Inhibitors of a \b-Galactofuranosidase.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4179
_journal_page_last               4189
_journal_paper_doi               10.1021/acs.joc.6b00514
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration synthesis
_chemical_formula_sum            'C26 H37 N O5'
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_space_group_IT_number           1
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_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                94.761(7)
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_cell_angle_gamma                97.721(8)
_cell_formula_units_Z            2
_cell_length_a                   5.5207(6)
_cell_length_b                   12.9380(12)
_cell_length_c                   17.1775(13)
_cell_measurement_reflns_used    2250
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.1220
_cell_measurement_theta_min      3.9960
_cell_volume                     1208.9(2)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELX (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1158
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_details
;
  1 omega    7.00   55.00   1.0000    1.7550
omega____ theta____ kappa____ phi______ frames
    -       18.3853  -99.0000  -60.0000 48

  2 omega  -21.00    5.00   1.0000    1.7550
omega____ theta____ kappa____ phi______ frames
    -      -18.6587  -99.0000  -30.0000 26

  3 omega  -25.00   20.00   1.0000    1.7550
omega____ theta____ kappa____ phi______ frames
    -      -18.6587  -99.0000   60.0000 45

  4 omega  -21.00    6.00   1.0000    1.7550
omega____ theta____ kappa____ phi______ frames
    -      -18.6587  -77.0000  150.0000 27

  5 omega  -38.00   21.00   1.0000    1.7550
omega____ theta____ kappa____ phi______ frames
    -       18.3853  -57.0000  150.0000 59

  6 omega   69.00   94.00   1.0000    1.7550
omega____ theta____ kappa____ phi______ frames
    -       18.3853  178.0000 -180.0000 25

  7 omega  -52.00   91.00   1.0000    1.7550
omega____ theta____ kappa____ phi______ frames
    -       18.3853    0.0000 -180.0000 143

  8 omega   38.00   84.00   1.0000    1.7550
omega____ theta____ kappa____ phi______ frames
    -       18.3853  178.0000  120.0000 46

;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0254547000
_diffrn_orient_matrix_UB_12      0.0311866000
_diffrn_orient_matrix_UB_13      -0.0314308000
_diffrn_orient_matrix_UB_21      -0.0986326000
_diffrn_orient_matrix_UB_22      0.0278169000
_diffrn_orient_matrix_UB_23      0.0091448000
_diffrn_orient_matrix_UB_31      0.0806979000
_diffrn_orient_matrix_UB_32      0.0366072000
_diffrn_orient_matrix_UB_33      0.0255573000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10240
_diffrn_reflns_point_group_measured_fraction_full 0.731
_diffrn_reflns_point_group_measured_fraction_max 0.593
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.177
_diffrn_reflns_theta_min         3.807
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.034
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1336 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     585
_refine_ls_number_reflns         7783
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0729
_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^)+(0.0771P)^2^+0.8151P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.1889
_reflns_Friedel_coverage         0.414
_reflns_Friedel_fraction_full    0.466
_reflns_Friedel_fraction_max     0.347
_reflns_number_gt                5717
_reflns_number_total             7783
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00514_si_002.cif
_cod_data_source_block           2b
_cod_database_code               4031998
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              39737
_shelx_hkl_checksum              76220