Synthesis of cis- and trans-α-l-[4.3.0]Bicyclo-DNA Monomers for Antisense Technology: Methods for the Diastereoselective Formation of Bicyclic Nucleosides
Stephen Hanessian; Benjamin R. Schroeder; Bradley L. Merner; Bin Chen; Eric E. Swayze; Punit P. Seth; Journal of Organic Chemistry 78 (2013) 9051–9063; doi:10.1021/jo401166q

data_4028589
_publ_section_title
;
 Synthesis of cis- and trans-\a-l-[4.3.0]Bicyclo-DNA Monomers for
 Antisense Technology: Methods for the Diastereoselective Formation of
 Bicyclic Nucleosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9051
_journal_page_last               9063
_journal_paper_doi               10.1021/jo401166q
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C19 H24 O7'
_chemical_formula_sum            'C19 H24 O7'
_chemical_formula_weight         364.38
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.05340(10)
_cell_length_b                   9.3596(2)
_cell_length_c                   31.6166(5)
_cell_measurement_reflns_used    9106
_cell_measurement_temperature    150
_cell_measurement_theta_max      71.88
_cell_measurement_theta_min      2.79
_cell_volume                     1791.31(6)
_computing_cell_refinement       'SAINT V7.34A(Bruker AXS, 2006)'
_computing_data_collection       'APEX2  (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A(Bruker AXS, 2006)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            24200
_diffrn_reflns_theta_full        72.82
_diffrn_reflns_theta_max         72.82
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  0.9097
_exptl_absorpt_correction_T_min  0.8405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), 1453 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.06(17)
_refine_ls_extinction_coef       0.0031(4)
_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   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3558
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.187
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0591P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0906
_reflns_number_gt                3282
_reflns_number_total             3558
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo401166q_si_002.cif
_cod_data_source_block           bent18
_cod_database_code               4028589