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_4026603
_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 unk
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             07-10-10
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 99.41(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.763(6)
_cell_length_b                   6.781(4)
_cell_length_c                   11.095(11)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     502.0(7)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_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      293
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2945
_diffrn_reflns_theta_full        25.002
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_min         3.053
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1207
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.000159
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.13P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0937
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0937
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1043
_reflns_number_total             1213
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.84
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          19(2)
_oxford_structure_analysis_title 'sx146 in P1'
_cod_data_source_file            jo201110z_si_004.cif
_cod_data_source_block           CRYSTALS_cif
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4026603