Stereocontrolled and Convergent Entry to CF2-Sialosides: Synthesis of CF2-Linked Ganglioside GM4
Go Hirai; Toru Watanabe; Kazunori Yamaguchi; Taeko Miyagi; Mikiko Sodeoka; Journal of the American Chemical Society 129 (2007) 15420–15421; doi:10.1021/ja075738w

data_4110296
_publ_section_title
;
 Stereocontrolled and Convergent Entry to CF2-Sialosides: Synthesis of
 CF2-Linked Ganglioside GM4
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15420
_journal_page_last               15421
_journal_paper_doi               10.1021/ja075738w
_journal_volume                  129
_journal_year                    2007
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C25 H33 F2 N O13, 1.5(H2 O)'
_chemical_formula_sum            'C25 H36 F2 N O14.5'
_chemical_formula_weight         620.55
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 95.5451(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0975(2)
_cell_length_b                   8.3422(2)
_cell_length_c                   28.8836(10)
_cell_measurement_reflns_used    196964
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.1
_cell_volume                     1462.33(8)
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_collection
;
 CrystalClear SM ver. 1.3.6 (Rigaku/MSC Inc., 2005)
;
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn 70 CCD'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  'confocal mirror'
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_av_sigmaI/netI    0.024
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            196964
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       needle
_exptl_crystal_F_000             654
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 The enantiomorph of the crystal was selected to 
 agree with the absolute structures of 
 sugers of A and B rings.
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         3574
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.2490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0835
_reflns_number_gt                3179
_reflns_number_total             3574
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja075738w-file003.cif
_cod_data_source_block           061124-Watanabe
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C25 H36 F2 N O14.50'
_cod_database_code               4110296