Study of the Endocyclic versus Exocyclic C-O Bond Cleavage Pathways of α- and β-Methyl Furanosides
Olivier St-Jean; Michel Prévost; Yvan Guindon; Journal of Organic Chemistry 78 (2013) 2935–2946; doi:10.1021/jo3027438

data_4028076
_publ_section_title
;
 Study of the Endocyclic versus Exocyclic C-O Bond Cleavage Pathways of
 \a- and \b-Methyl Furanosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2935
_journal_page_last               2946
_journal_paper_doi               10.1021/jo3027438
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C40 H40 O6 S'
_chemical_formula_sum            'C40 H40 O6 S'
_chemical_formula_weight         648.78
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                66.010(3)
_cell_angle_beta                 68.622(3)
_cell_angle_gamma                67.713(3)
_cell_formula_units_Z            1
_cell_length_a                   8.9185(11)
_cell_length_b                   10.0484(13)
_cell_length_c                   11.7694(15)
_cell_measurement_reflns_used    6446
_cell_measurement_temperature    200
_cell_measurement_theta_max      26.19
_cell_measurement_theta_min      2.31
_cell_volume                     863.60(19)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 v2.4-0 (Bruker AXS, 2007)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_source         'x-ray sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17729
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        1.20
_diffrn_standards_interval_time  900
_diffrn_standards_number         308
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_correction_T_min  0.8850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), 3923 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         7900
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0317P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0752
_reflns_number_gt                6726
_reflns_number_total             7900
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo3027438_si_002.cif
_cod_data_source_block           guin58
_cod_database_code               4028076