Synthesis of Polyhydroxylated 2H-Azirines and 2-Halo-2H-azirines from 3-Azido-2,3-dideoxyhexopyranoses by Alkoxyl Radical Fragmentation
Carmen R. Alonso-Cruz; Alan R. Kennedy; María S. Rodríguez; Ernesto Suárez; Journal of Organic Chemistry 73 (2008) 4116–4122; doi:10.1021/jo800182y

data_4023426
_publ_section_title
;
 Synthesis of Polyhydroxylated 2H-Azirines and 2-Halo-2H-azirines
 from 3-Azido-2,3-dideoxyhexopyranoses by Alkoxyl Radical Fragmentation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4116
_journal_page_last               4122
_journal_paper_doi               10.1021/jo800182y
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C14 H25 N O4 Si'
_chemical_formula_weight         299.44
_chemical_name_systematic
;
 ?
;
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.529(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.4478(8)
_cell_length_b                   6.2864(3)
_cell_length_c                   16.1368(8)
_cell_measurement_reflns_used    1738
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      1.02
_cell_volume                     1660.74(14)
_computing_data_collection       'Collect & Denzo'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Shelxs
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.053
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8917
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3245
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0147P)^2^+0.9860P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                2690
_reflns_number_total             3245
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800182y-File001.cif
_cod_data_source_block           26
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4023426