4,6-O-[1-Cyano-2-(2-iodophenyl)ethylidene] Acetals. Improved Second-Generation Acetals for the Stereoselective Formation of β-D-Mannopyranosides and Regioselective Reductive Radical Fragmentation to β-D-Rhamnopyranosides. Scope and Limitations
David Crich; Albert A. Bowers; Journal of Organic Chemistry 71 (2006) 3452–3463; doi:10.1021/jo0526688

data_4021653
_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
;
 4,6-O-[1-Cyano-2-(2-iodophenyl)ethylidene] Acetals.
 Improved Second-Generation Acetals for the Stereoselective
 Formation of \b-D-Mannopyranosides and Regioselective Reductive
 Radical Fragmentation to \b-D-Rhamnopyranosides.
 Scope and Limitations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3452
_journal_page_last               3463
_journal_paper_doi               10.1021/jo0526688
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C47 H52 I N10 O12'
_chemical_formula_weight         1075.89
_chemical_melting_point          386.6(15)
_chemical_name_systematic
; 
Methyl-4-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]
ethylidene-\b-D-mannopyranosyl)-2,3-O-isopropylidene-\a-L-rhamnopyranoside 
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.076(3)
_cell_angle_beta                 99.448(3)
_cell_angle_gamma                90.430(3)
_cell_formula_units_Z            2
_cell_length_a                   11.073(2)
_cell_length_b                   11.844(2)
_cell_length_c                   17.130(3)
_cell_measurement_temperature    298(2)
_cell_volume                     2126.1(7)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.918
_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  0.0451
_diffrn_reflns_av_sigmaI/netI    0.1129
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19907
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.26
_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7011
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1022
_exptl_crystal_size_max          '0.482 mm'
_exptl_crystal_size_mid          '0.234 mm'
_exptl_crystal_size_min          '0.106 mm'
_refine_diff_density_max         1.084
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.024(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1021
_refine_ls_number_reflns         16795
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.909
_refine_ls_R_factor_all          0.1280
_refine_ls_R_factor_gt           0.0686
_refine_ls_shift/su_max          1.080
_refine_ls_shift/su_mean         0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0739P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1656
_reflns_number_gt                8950
_reflns_number_total             16795
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0526688si20060301_115633.cif
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '112-115_C' was changed to
'386.6(15)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4021653