Aluminium triflate catalysed O-glycosidation: temperature-switched selective Ferrier rearrangement or direct addition with alcohols.
Williams, D Bradley G; Simelane, Sandile B.; Kinfe, Henok H.; Organic & biomolecular chemistry 10 (2012) 5636–5642; doi:10.1039/c2ob25540e

data_7152424
_publ_section_title
;
 Aluminium triflate catalysed O-glycosidation: temperature-switched
 selective Ferrier rearrangement or direct addition with alcohols.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5636
_journal_page_last               5642
_journal_paper_doi               10.1039/c2ob25540e
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H20 O6'
_chemical_formula_sum            'C20 H20 O6'
_chemical_formula_weight         356.36
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2010-10-05T20:47:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 112.4100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.7271(18)
_cell_length_b                   5.6497(4)
_cell_length_c                   13.2772(9)
_cell_measurement_reflns_used    33930
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.45
_cell_measurement_theta_min      1.66
_cell_volume                     1784.1(2)
_computing_cell_refinement       'SAINT-plus (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker X8 ApexII 4K Kappa CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33930
_diffrn_reflns_theta_full        28.45
_diffrn_reflns_theta_max         28.45
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_correction_T_min  0.9345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4465
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.4878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0794
_reflns_number_gt                4362
_reflns_number_total             4465
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25540e.txt
_cod_data_source_block           mo_10bo_sand5_0m
_cod_original_sg_symbol_H-M      C2
_cod_database_code               7152424