A diastereoselective synthesis of 5'-substituted-uridine derivatives.
Fer, Mickaël J; Doan, Pierre; Prangé, Thierry; Calvet-Vitale, Sandrine; Gravier-Pelletier, Christine; The Journal of organic chemistry 79 (2014) 7758–7765; doi:10.1021/jo501410m

data_4029833
_publ_section_title
;
 A diastereoselective synthesis of 5'-substituted-uridine derivatives.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7758
_journal_page_last               7765
_journal_paper_doi               10.1021/jo501410m
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C22 H40 N2 O6 Si2'
_chemical_formula_weight         484.74
_chemical_name_systematic
;
C5'-C6'[S]epoxide of O2',O3' di-terbutyldimethylsilyl uridine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 93.65(5)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   17.049(2)
_cell_length_b                   6.880(1)
_cell_length_c                   34.497(3)
_cell_measurement_temperature    100(2)
_cell_volume                     4038.2(9)
_computing_data_collection       'MXCUBE (ESRF, 2014)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2010)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.521
_diffrn_measured_fraction_theta_max 0.780
_diffrn_measurement_device_type  'MAR Research CCD'
_diffrn_measurement_method       rotation
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.964
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.521
_diffrn_reflns_Laue_measured_fraction_max 0.780
_diffrn_reflns_number            21775
_diffrn_reflns_point_group_measured_fraction_full 0.284
_diffrn_reflns_point_group_measured_fraction_max 0.431
_diffrn_reflns_theta_full        35.888
_diffrn_reflns_theta_max         30.683
_diffrn_reflns_theta_min         1.626
_diffrn_source                   'BM 14 beamline'
_exptl_absorpt_coefficient_mu    0.378
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       needle
_exptl_crystal_F_000             1572
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.598
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     844
_refine_ls_number_reflns         4150
_refine_ls_number_restraints     829
_refine_ls_restrained_S_all      2.524
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0945
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.018
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2385
_refine_ls_wR_factor_ref         0.2389
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                4130
_reflns_number_total             4150
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo501410m_si_001.cif
_cod_data_source_block           epoxide4a
_cod_depositor_comments          'Adding full bibliography for 4029833.cif.'
_cod_original_cell_volume        4038.2(8)
_cod_database_code               4029833