Transient imine as a directing group for the Pd-catalyzed anomeric C(sp<sup>3</sup>)-H arylation of 3-aminosugars.
Ghouilem, Juba; Bazzi, Sokna; Grimblat, Nicolas; Retailleau, Pascal; Gandon, Vincent; Messaoudi, Samir; Chemical communications (Cambridge, England) 59 (2023) 2497–2500; doi:10.1039/d3cc00046j

data_7131267
_publ_section_title
;
 Transient imine as a directing group for the Pd-catalyzed anomeric
 C(sp<sup>3</sup>)-H arylation of 3-aminosugars.
;
_journal_issue                   17
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2497
_journal_page_last               2500
_journal_paper_doi               10.1039/d3cc00046j
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C27 H29 N3 O3'
_chemical_formula_sum            'C27 H29 N3 O3'
_chemical_formula_weight         443.53
_chemical_name_systematic
2R,3S,4S,6S)-4-azido-3-(benzyloxy)-2-((benzyloxy)methyl)-6-(p-tolyl)tetrahydro-2H-pyran
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-12-09 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8747(2)
_cell_length_b                   10.5771(4)
_cell_length_c                   44.7202(16)
_cell_measurement_reflns_used    9625
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.9290
_cell_measurement_theta_min      2.1430
_cell_volume                     2305.78(15)
_computing_cell_refinement       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            25032
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.341
_diffrn_reflns_theta_min         2.130
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.75a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             944
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: deuterated chloroform'
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.7(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4181
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0431P)^2^+0.2843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3483
_reflns_number_total             4183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00046j2.cif
_cod_data_source_block           3a-JG-SArN3-Mo-123K
_cod_depositor_comments
'Adding full bibliography for 7131267--7131268.cif.'
_cod_database_code               7131267
_shelx_res_checksum              58161
_shelx_hkl_checksum              58373