Diastereoselective C-C Bond Formation at C-5 of Vinyl Sulfone-Modified Hex-5-enofuranosyl Carbohydrates: Diversity-Oriented Synthesis of Branched-Chain Sugars and Beyond
Indrajit Das; Tarun K. Pal; Cheravakkattu G. Suresh; Tanmaya Pathak; Journal of Organic Chemistry 72 (2007) 5523–5533; doi:10.1021/jo062373+

data_4024044
_publ_contact_author_address
'Department of Chemistry, IIT, Kharagpur 721 302, India'
_publ_contact_author_email       tpathak@chem.iitkgp.ernet.in
_publ_contact_author_name        'Tanmaya Pathak'
_publ_section_title
;
 Diastereoselective C-C Bond Formation at C-5 of Vinyl Sulfone-Modified
 Hex-5-enofuranosyl Carbohydrates: Diversity-Oriented Synthesis of
 Branched-Chain Sugars and Beyond
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5523
_journal_page_last               5533
_journal_paper_doi               10.1021/jo062373+
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C28 H30 O11 S'
_chemical_formula_sum            'C28 H30 O11 S'
_chemical_formula_weight         574.58
_space_group_IT_number           146
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_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                120.00
_cell_formula_units_Z            9
_cell_length_a                   27.9054(14)
_cell_length_b                   27.9054(14)
_cell_length_c                   9.5055(5)
_cell_measurement_reflns_used    9245
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.25
_cell_measurement_theta_min      1.46
_cell_volume                     6410.4(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       '\w 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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9245
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         1.46
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count n/a
_diffrn_standards_number         n/a
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.519
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'SADABS  (Bruker-AXS, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2718
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.11(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4073
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0742P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1157
_reflns_number_gt                3635
_reflns_number_total             4073
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062373+si20061117_031806.cif
_cod_data_source_block           sep9
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               4024044