Synthesis of the Aminocyclitol Units of (-)-Hygromycin A and Methoxyhygromycin from myo-Inositol
Bharat P. Gurale; Mysore S. Shashidhar; Rajesh G. Gonnade; Journal of Organic Chemistry 77 (2012) 5801–5807; doi:10.1021/jo300444b

data_4027257
_publ_section_title
;
 Synthesis of the Aminocyclitol Units of (-)-Hygromycin A and
 Methoxyhygromycin from myo-Inositol
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5801
_journal_page_last               5807
_journal_paper_doi               10.1021/jo300444b
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C31 H31 N3 O8'
_chemical_formula_sum            'C31 H31 N3 O8'
_chemical_formula_weight         573.59
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.580(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4388(5)
_cell_length_b                   26.4633(17)
_cell_length_c                   14.6237(10)
_cell_measurement_reflns_used    5848
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.389
_cell_measurement_theta_min      2.698
_cell_volume                     2873.1(3)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    'SHELXTL, ORTEP3,MERCURY1.2.1'
_computing_publication_material  'SHELXTL, PLATON'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.799
_diffrn_measured_fraction_theta_max 0.799
_diffrn_measurement_device       'BRUKER SMART APEX'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'Omega and phi 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  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16623
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9954
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       needle
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(8)
_refine_ls_extinction_coef       0.0027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     799
_refine_ls_number_reflns         6962
_refine_ls_number_restraints     115
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0385P)^2^+0.3767P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                5841
_reflns_number_total             6962
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300444b_si_006.cif
_cod_data_source_block           compound_18
_cod_database_code               4027257