Synthesis of 1',2'-cis-Nucleoside Analogues: Evidence of Stereoelectronic Control for SN2 Reactions at the Anomeric Center of Furanosides
Michel Prévost; Olivier St-Jean; Yvan Guindon; Journal of the American Chemical Society 132 (2010) 12433–12439; doi:10.1021/ja104429y

data_4103010
_publ_contact_author_address
;
      IRCM
      110 ouest, Avenue des Pins     
      Montr\'eal, Qu\'ebec
      Canada H2W 1R7
;
_publ_contact_author_email       guindoy@ircm.qc.ca
_publ_contact_author_fax         '+1 514 987 5789'
_publ_contact_author_name        'Dr. Yvan Guindon'
_publ_contact_author_phone       '+1 514 987 5788'
_publ_section_title
;
 Synthesis of 1',2'-cis-Nucleoside Analogues: Evidence of Stereoelectronic
 Control for SN2 Reactions at the Anomeric Center of Furanosides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12433
_journal_page_last               12439
_journal_paper_doi               10.1021/ja104429y
_journal_volume                  132
_journal_year                    2010
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C14 H25 N3 O3 Si'
_chemical_formula_sum            'C14 H25 N3 O3 Si'
_chemical_formula_weight         311.46
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 102.276(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   32.562(8)
_cell_length_b                   10.769(3)
_cell_length_c                   10.969(3)
_cell_measurement_reflns_used    8047
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      23.70
_cell_measurement_theta_min      2.56
_cell_volume                     3758.4(17)
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      240
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker Smart 2000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray Sealed Tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            44509
_diffrn_reflns_theta_full        31.45
_diffrn_reflns_theta_max         31.45
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_correction_T_min  0.7828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.101
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         5944
_refine_ls_number_restraints     115
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.0860
_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^)+(0.1903P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2967
_refine_ls_wR_factor_ref         0.3362
_reflns_number_gt                2960
_reflns_number_total             5944
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja104429y_si_002.cif
_cod_data_source_block           guin51
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to the
built-in table from CIF Core dictionary named 'cif_core.dic' version
2.4.1 from 2010-06-29 (36 times).

'_geom_angle_publ_flag' value 'Y'
changed to 'y' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (63
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according
to the built-in table from CIF Core dictionary named 'cif_core.dic'
version 2.4.1 from 2010-06-29 (87 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3758.4(16)
_cod_database_code               4103010