On the Use of 3,5-O-Benzylidene and 3,5-O-(Di-tert-butylsilylene)-2-O-benzylarabinothiofuranosides and Their Sulfoxides as Glycosyl Donors for the Synthesis of β-Arabinofuranosides: Importance of the Activation Method
David Crich; Christian Marcus Pedersen; Albert A. Bowers; Donald J. Wink; Journal of Organic Chemistry 72 (2007) 1553–1565; doi:10.1021/jo061440x

data_4022589
_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
;
 On the Use of 3,5-O-Benzylidene and
 3,5-O-(Di-tert-butylsilylene)-2-O-benzylarabinothiofuranosides and
 Their Sulfoxides as Glycosyl Donors for the Synthesis of
 \b-Arabinofuranosides: Importance of the Activation Method
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1553
_journal_page_last               1565
_journal_paper_doi               10.1021/jo061440x
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C26 H26 O4 S'
_chemical_formula_weight         434.53
_chemical_name_systematic
; 
p-Cresyl 2-O-benzyl-3,5-di-O-benzylidene-1-thio-/a/-D-arabinofuranoside 

;
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.192(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.7318(5)
_cell_length_b                   11.6928(13)
_cell_length_c                   20.242(2)
_cell_measurement_temperature    296(2)
_cell_volume                     1120.0(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      296(2)
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_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  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0744
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10537
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.01
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.505
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.141
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.856
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5026
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.856
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0278P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0823
_reflns_number_gt                3234
_reflns_number_total             5026
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061440xsi20060711_054210.cif
_cod_data_source_block           Compound6
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022589