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_7251146
_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         'C20 H21 N O5, 0.667(H2 O)'
_chemical_formula_sum            'C20 H22.33 N O5.67'
_chemical_formula_weight         367.39
_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             2025-04-02
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-04-03 deposited with the CCDC.	2025-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.955(3)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   17.9551(12)
_cell_length_b                   7.5298(5)
_cell_length_c                   20.8678(14)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    295.00
_cell_measurement_theta_max      21.42
_cell_measurement_theta_min      2.30
_cell_volume                     2786.9(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      295.00
_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 0.999
_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  0.0841
_diffrn_reflns_av_unetI/netI     0.0937
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            43624
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.393
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5788
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0994 before and 0.0733 after correction.
The Ratio of minimum to maximum transmission is 0.7765.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 2059 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     727
_refine_ls_number_reflns         10353
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.1392
_refine_ls_R_factor_gt           0.0820
_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^)+(0.0416P)^2^+3.1191P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.1756
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6521
_reflns_number_total             10353
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra05811b2.cif
_cod_data_source_block           16b
_cod_database_code               7251146
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.994
_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 O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O17(H17A,H17B,O16,H16A,H16B)
2.b Ternary CH refined with riding coordinates:
 C42(H42), C43(H43), C22(H22), C25(H25), C2(H2), C3(H3), C44(H44), C41(H41),
 C45(H45), C21(H21), C24(H24), C1(H1), C23(H23), C4(H4A), C5(H5A)
2.c Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C46(H46A,H46B), C47(H47A,H47B), C26(H26A,H26B), C7(H7A,H7B),
 C6(H6A,H6B)
2.d Aromatic/amide H refined with riding coordinates:
 C20(H20), C60(H60), C16(H16), C56(H56), C36(H36), C19(H19), C29(H29), C9(H9A),
  C40(H40), C58(H58), C59(H59), C17(H17), C33(H33), C13(H13), C57(H57),
 C49(H49), C18(H18), C53(H53), C37(H37), C30(H30), C32(H32), C39(H39), C38(H38),
  C10(H10A), C11(H11), C52(H52), C31(H31), C12(H12), C51(H51), C50(H50)
2.e Idealised tetrahedral OH refined as rotating group:
 O9(H9), O14(H14), O5(H5), O4(H4), O15(H15), O10(H10)
;
_shelx_res_checksum              99010
_olex2_submission_special_instructions 'No special instructions were received'