A Modular Approach to Aryl-C-ribonucleosides via the Allylic Substitution and Ring-Closing Metathesis Sequence. A Stereocontrolled Synthesis of All Four α-/β- and d-/l-C-Nucleoside Stereoisomers
Jan Štambaský; Vojtěch Kapras; Martin Štefko; Ondřej Kysilka; Michal Hocek; Andrei V. Malkov; Pavel Kočovský; Journal of Organic Chemistry 76 (2011) 7781–7803; doi:10.1021/jo201110z

data_4026602
_publ_section_title
;
 A Modular Approach to Aryl-C-ribonucleosides via the Allylic Substitution
 and Ring-Closing Metathesis Sequence. A Stereocontrolled Synthesis of All
 Four \a-/\b- and d-/l-C-Nucleoside Stereoisomers
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7781
_journal_page_last               7803
_journal_paper_doi               10.1021/jo201110z
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C11 H14 O4'
_chemical_formula_sum            'C11 H14 O4'
_chemical_formula_weight         210.23
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             07-06-21
_audit_creation_method           CRYSTALS_ver_12.83
_cell_angle_alpha                90
_cell_angle_beta                 99.636(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.7734(4)
_cell_length_b                   6.7395(4)
_cell_length_c                   11.0228(7)
_cell_measurement_reflns_used    3488
_cell_measurement_temperature    100
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3
_cell_volume                     496.08(5)
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'APEX2 (Bruker, 2006)'
_computing_molecular_graphics    Mercury
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker Nonius APEX2 CCD diffractometer'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4583
_diffrn_reflns_theta_full        25.267
_diffrn_reflns_theta_max         28.390
_diffrn_reflns_theta_min         1.874
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.16
_refine_ls_extinction_coef       24(6)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9544
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         1242
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.000177
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 30.8 48.1 24.4 6.54 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0704
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0704
_reflns_limit_h_max              7
_reflns_limit_h_min              -9
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1204
_reflns_number_total             1242
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          1.621(14)
_oxford_structure_analysis_title 'sx140 in P2(1)'
_cod_data_source_file            jo201110z_si_002.cif
_cod_data_source_block           sx140_publish
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4026602