Synthesis of Isoxazolin-5-one Glucosides by a Cascade Reaction
Tobias Becker; Helmar Görls; Gerhard Pauls; Roland Wedekind; Marco Kai; Stephan H. von Reuß; Wilhelm Boland; Journal of Organic Chemistry 78 (2013) 12779–12783; doi:10.1021/jo4023155

data_4028884
_publ_contact_author
;
        Wilhelm Boland
        Max-Planck-Institut for Chemical Ecology
        Tatzendpromenade 1a
        D-07745 Jena
        Germany
;
_publ_contact_author_email       'boland@ice.mpg.de '
_publ_contact_author_fax         '+049-03641-643665 '
_publ_contact_author_phone       '+049-03641-643663 '
_publ_section_title
;
 Synthesis of Isoxazolin-5-one Glucosides by a Cascade Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12779
_journal_page_last               12783
_journal_paper_doi               10.1021/jo4023155
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C37 H37 N O7'
_chemical_formula_sum            'C37 H37 N O7'
_chemical_formula_weight         607.68
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.609(2)
_cell_angle_beta                 96.556(2)
_cell_angle_gamma                104.520(2)
_cell_formula_units_Z            2
_cell_length_a                   10.6443(5)
_cell_length_b                   12.4845(6)
_cell_length_c                   12.8966(6)
_cell_measurement_reflns_used    70532
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      2.72
_cell_volume                     1576.38(13)
_computing_cell_refinement       DENZO
_computing_data_collection       COLLECT
_computing_data_reduction        DENZO
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_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  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            73797
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       prism
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
'Flack H D (1983),6266 Friedel pairs Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     827
_refine_ls_number_reflns         13169
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0391P)^2^+0.2017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0730
_reflns_number_gt                12360
_reflns_number_total             13169
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4023155_si_002.cif
_cod_data_source_block           fo5082
_cod_database_code               4028884