Synthesis of CH2-linked alpha(2,3)sialylgalactose analogue: on the stereoselectivity of the key Ireland-Claisen rearrangement.
Watanabe, Toru; Hirai, Go; Kato, Marie; Hashizume, Daisuke; Miyagi, Taeko; Sodeoka, Mikiko; Organic letters 10 (2008) 4167–4170; doi:10.1021/ol801519j

data_1504850
_publ_section_title
;
 Synthesis of CH2-linked alpha(2,3)sialylgalactose analogue: on the
 stereoselectivity of the key Ireland-Claisen rearrangement.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4167
_journal_page_last               4170
_journal_paper_doi               10.1021/ol801519j
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C25 H35 N O13, C H4 O, H2 O'
_chemical_formula_sum            'C26 H41 N O15'
_chemical_formula_weight         607.60
_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                 95.6566(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0684(2)
_cell_length_b                   8.3967(3)
_cell_length_c                   29.0292(8)
_cell_measurement_reflns_used    18893
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.81
_cell_volume                     1471.97(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-2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0375
_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            18880
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041
_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     410
_refine_ls_number_reflns         3580
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0492P)^2^+0.3002P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                3054
_reflns_number_total             3580
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol801519j_si_001.cif
_cod_data_source_block           13174
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1504850