C2-ketonylation of carbohydrates via excited-state palladium-catalyzed 1,2-spin-center shift
Zhao, Gaoyuan; Mukherjee, Upasana; Zhou, Lin; Wu, Yue; Yao, Wang; Mauro, Jaclyn N.; Liu, Peng; Ngai, Ming-Yu; Chemical Science  (2022) –; doi:10.1039/D2SC01042A

data_1566957
_publ_section_title
;
 C2-ketonylation of carbohydrates via excited-state palladium-catalyzed
 1,2-spin-center shift
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC01042A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C40 H38 O10'
_chemical_formula_weight         678.70
_chemical_name_systematic
(2R,3S,4R,5S,6R)-6-((benzoyloxy)methyl)-3-(3,3-dimethyl-2-oxobutyl)tetrahydro-2H-pyran-2,4,5-triyl
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2022-01-15 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                97.644(2)
_cell_angle_beta                 101.994(2)
_cell_angle_gamma                104.537(2)
_cell_formula_units_Z            4
_cell_length_a                   13.5907(8)
_cell_length_b                   15.0346(9)
_cell_length_c                   18.9632(12)
_cell_measurement_reflns_used    9179
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      23.49
_cell_measurement_theta_min      2.19
_cell_volume                     3598.0(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            105687
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.310
_diffrn_reflns_theta_min         1.427
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       cut-block
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 7762 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1801
_refine_ls_number_reflns         35654
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0412P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.1022
_reflns_Friedel_coverage         0.994
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                20893
_reflns_number_total             35654
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01042a2.cif
_cod_data_source_block           Per-Bz-C2-deoxypivaloylmethyl-a-Glu
_cod_database_code               1566957
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              3650