Efficient Dehydrative Sialylation of C-4-Aminated Sialyl-Hemiketal Donors with Ph2SO/Tf2O
Deju Ye; Wenfeng Liu; Dengyou Zhang; Enguang Feng; Hualiang Jiang; Hong Liu; Journal of Organic Chemistry 74 (2009) 1733–1735; doi:10.1021/jo802396a

data_4024333
_publ_contact_author             'Deju Ye'
_publ_contact_author_email       yedeju@mail.shcnc.ac.cn
_publ_section_title
;
Efficient Dehydrative Sialylation of C-4-Aminated Sialyl-Hemiketal Donors
with Ph2SO/Tf2O
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1733
_journal_page_last               1735
_journal_paper_doi               10.1021/jo802396a
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H36 N2 O12'
_chemical_formula_weight         532.54
_chemical_name_systematic
; 
 Methyl [2-methyl 5-acetamido-4-morpholin-4-yl-7,8,9-
tri-O-acetyl-3,5-dideoxy-D-glycerol-alfa-D-galacto-non-2-
ulopyranosid]onate 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8651(12)
_cell_length_b                   11.3312(13)
_cell_length_c                   24.133(3)
_cell_measurement_reflns_used    3645
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      52.098
_cell_measurement_theta_min      4.932
_cell_volume                     2697.6(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1435
_diffrn_reflns_av_sigmaI/netI    0.0829
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14773
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78894
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1136
_exptl_crystal_preparation       methanol
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.441
_exptl_crystal_size_min          0.271
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         2997
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0858P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1447
_reflns_number_gt                2409
_reflns_number_total             2997
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802396a_si_001.cif
_cod_data_source_block           dddcsyn02
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4024333