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_4027256
_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_formula_moiety         'C14 H17 N3 O5'
_chemical_formula_sum            'C14 H17 N3 O5'
_chemical_formula_weight         307.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_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                91.7140(10)
_cell_angle_beta                 103.3900(10)
_cell_angle_gamma                117.7640(10)
_cell_formula_units_Z            4
_cell_length_a                   10.2239(8)
_cell_length_b                   10.7231(9)
_cell_length_c                   15.4953(13)
_cell_measurement_reflns_used    6948
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.18
_cell_volume                     1443.5(2)
_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      297(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0136
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13362
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.9691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'bruker sadabs'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         5061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0472P)^2^+0.3495P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0987
_reflns_number_gt                4416
_reflns_number_total             5061
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300444b_si_005.cif
_cod_data_source_block           compound_12
_cod_database_code               4027256