Addition of Lithiated C-Nucleophiles to 2,3-O-Isopropylidene-D-erythronolactone: Stereoselective Formation of a Furanose C-Disaccharide
Jason L. McCartney; Christopher T. Meta; Robert M. Cicchillo; Matthew D. Bernardina; Timothy R. Wagner; Peter Norris; Journal of Organic Chemistry 68 (2003) 10152–10155; doi:10.1021/jo0350256

data_4022543
_publ_contact_author_address
; 
Department of Chemistry
Youngstown State University
One University Plaza
Youngstown, OH  44555
;
_publ_contact_author_email       Pnorris@cc.ysu.edu
_publ_contact_author_fax         '330 941 1579'
_publ_contact_author_name        'Professor Peter Norris'
_publ_contact_author_phone       '330 941 1553'
_publ_section_title
;
 Addition of Lithiated C-Nucleophiles to
 2,3-O-Isopropylidene-D-erythronolactone: Stereoselective Formation
 of a Furanose C-Disaccharide
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10152
_journal_page_last               10155
_journal_paper_doi               10.1021/jo0350256
_journal_volume                  68
_journal_year                    2003
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H18 O3 S2'
_chemical_formula_sum            'C11 H18 O3 S2'
_chemical_formula_weight         262.37
_chemical_name_systematic
; 
 (2S,3S,4R) 3,4-O-isopropylidene-2-phenyl-tetrahydrofuran-3,4-diol 
;
_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_date             'July 8, 2003'
_audit_creation_method
'from SHELXTL97 CIF and IUCr SHELXTL97-template'
_audit_update_record
;
Final CIF - passed ???
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.940(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.5719(6)
_cell_length_b                   9.6793(5)
_cell_length_c                   10.2878(5)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      37.281
_cell_measurement_theta_min      11.134
_cell_volume                     644.60(7)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker XSCANS'
_computing_molecular_graphics    'Bruker SHELXP'
_computing_publication_material  'Bruker SHELXP'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1962
_diffrn_reflns_theta_full        57.16
_diffrn_reflns_theta_max         57.16
_diffrn_reflns_theta_min         4.36
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.678
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XPREP: Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.020(19)
_refine_ls_extinction_coef       0.0238(18)
_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   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         1680
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0305
_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^)+(0.0610P)^2^+0.0295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                1649
_reflns_number_total             1680
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0350256si20030716_093454.cif
_cod_data_source_block           jmcart2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022543