Direct Stereocontrolled Synthesis of 3-Amino-3-deoxy-β-Mannopyranosides: Importance of the Nitrogen Protecting Group on Stereoselectivity
David Crich; Huadong Xu; Journal of Organic Chemistry 72 (2007) 5183–5192; doi:10.1021/jo070473p

data_4023977
_publ_contact_author_address
; Department of Chemistry (m/c 111)
  University of Illinois at Chicago
  845 W. Taylor Street
  Chicago, Illinois 60607
  USA
;
_publ_contact_author_email       dcrich@uic.edu
_publ_contact_author_fax         (312)9960431
_publ_contact_author_name        'Dr. David A. Crich'
_publ_contact_author_phone       (312)9965189
_publ_section_title
;
 Direct Stereocontrolled Synthesis of
 3-Amino-3-deoxy-\b-Mannopyranosides: Importance of the Nitrogen
 Protecting Group on Stereoselectivity
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5183
_journal_page_last               5192
_journal_paper_doi               10.1021/jo070473p
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C21 H19 I N4 O4 S'
_chemical_formula_sum            'C21 H19 I N4 O4 S'
_chemical_formula_weight         550.36
_chemical_name_systematic
; 
Phenyl 3-azido-3-deoxy-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-/a/-
D-thiomannopyranoside
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9728(4)
_cell_length_b                   9.5086(5)
_cell_length_c                   29.1573(16)
_cell_measurement_temperature    293(2)
_cell_volume                     2210.4(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            20783
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         1.40
_exptl_absorpt_coefficient_mu    1.579
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          '0.17 mm'
_exptl_crystal_size_mid          '0.17 mm'
_exptl_crystal_size_min          '0.12 mm'
_refine_diff_density_max         1.176
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.184
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0675P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1226
_reflns_number_gt                4283
_reflns_number_total             5177
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070473psi20070309_073454.cif
_cod_data_source_block           Compound15
_cod_database_code               4023977