Acid-catalysed rearrangement of acyl groups: synthesis of β-d-gluco aminocyclopentitols and carbanucleoside derivatives.
Halder, Tapas; Hore, Ratul; Das, Susanta; Sett, Subhadip; Maity, Joykrishna; RSC advances 15 (2025) 40390–40399; doi:10.1039/d5ra05811b

data_7251145
_publ_section_title
;
 Acid-catalysed rearrangement of acyl groups: synthesis of &#x3b2;-d-gluco
 aminocyclopentitols and carbanucleoside derivatives.
;
_journal_issue                   48
_journal_name_full               'RSC advances'
_journal_page_first              40390
_journal_page_last               40399
_journal_paper_doi               10.1039/d5ra05811b
_journal_volume                  15
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H19 N O5, H2 O'
_chemical_formula_sum            'C15 H21 N O6'
_chemical_formula_weight         311.33
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-04-18
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7205)
;
_audit_update_record
;
2025-04-21 deposited with the CCDC.	2025-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.408(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.1486(11)
_cell_length_b                   11.036(2)
_cell_length_c                   14.010(3)
_cell_measurement_reflns_used    1023
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      20.39
_cell_measurement_theta_min      2.36
_cell_volume                     793.7(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11104
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.035
_diffrn_reflns_theta_min         2.352
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5304
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1844 before and 0.0734 after correction.
The Ratio of minimum to maximum transmission is 0.7115.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 816 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3459
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0488P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1048
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                2293
_reflns_number_total             3459
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra05811b2.cif
_cod_data_source_block           15a
_cod_database_code               7251145
_shelx_shelxl_version_number     2019/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O6(H6C,H6D)
2.b Ternary CH refined with riding coordinates:
 C5(H5), C1(H1), C4(H4), C2(H2A), C3(H3A)
2.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B)
2.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C10(H10), C11(H11), C12(H12)
2.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.f Idealised tetrahedral OH refined as rotating group:
 O3(H3), O2(H2)
;
_shelx_res_checksum              48207
_olex2_submission_special_instructions 'No special instructions were received'