Highly Diastereoselective Synthesis of a HCV NS5B Nucleoside Polymerase Inhibitor.
Zhong, Yong-Li; Cleator, Ed; Liu, Zhijian; Yin, Jianguo; Morris, William J.; Alam, Mahbub; Bishop, Brian; Dumas, Aaron M.; Edwards, John; Goodyear, Adrian; Mullens, Peter; Song, Zhiguo Jake; Shevlin, Michael; Thaisrivongs, David A.; Li, Hongming; Sherer, Edward C.; Cohen, Ryan D.; Yin, Jingjun; Tan, Lushi; Yasuda, Nobuyoshi; Limanto, John; Davies, Antony; Campos, Kevin R.; The Journal of organic chemistry 84 (2019) 4780–4795; doi:10.1021/acs.joc.8b02500

data_4035938
_publ_section_title
;
 Highly Diastereoselective Synthesis of a HCV NS5B Nucleoside Polymerase
 Inhibitor.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4780
_journal_page_last               4795
_journal_paper_doi               10.1021/acs.joc.8b02500
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H30 O4 Si'
_chemical_formula_sum            'C17 H30 O4 Si'
_chemical_formula_weight         326.503
_chemical_name_systematic
(3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methyl-3-((triisopropylsilyl)ethynyl)dihydro-furan-2(3H)-one
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_creation_date             2013-06-18
_audit_creation_method           'merge of exptl & shelxl CIFs via mrlcif'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8460(6)
_cell_length_b                   10.5118(7)
_cell_length_c                   20.6078(14)
_cell_measurement_radiation      'Cu K\a'
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.6343
_cell_measurement_theta_min      4.2908
_cell_volume                     1916.3(2)
_computing_cell_refinement       'SAINT V7.68A'
_computing_data_collection       'SAINT V7.68A'
_computing_data_reduction        'SAINT V7.68A'
_computing_molecular_graphics
;
ORTEP3 (Johnson,2000), PLATON (Spek,1990),
PSPLUTO (local version of Motherwell's program)
;
_computing_publication_material  'locally developed programs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 8.333
_diffrn_detector_type            'Bruker APEXII'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_details
;
crystal to CCD distance 5.5000 cm
 generator setting 45.00 KV, 0.65 ma
 frame size 512 pixels square
;
_diffrn_measurement_device_type  'Bruker \k-geometry diffractometer'
_diffrn_measurement_method       'omega, phi oscillation scans'
_diffrn_measurement_specimen_support 'micromount / oil'
_diffrn_radiation_collimation    '0.1mm pinhole'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0147
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26310
_diffrn_reflns_theta_full        66.66
_diffrn_reflns_theta_max         66.66
_diffrn_reflns_theta_min         4.29
_diffrn_source                   'sealed-tube X-ray generator'
_diffrn_source_power             0.65
_diffrn_source_size              'micro-focus filament'
_diffrn_source_target            Cu
_diffrn_source_type              Bruker
_diffrn_source_voltage           45.00
_exptl_absorpt_coefficient_mu    1.1969
_exptl_absorpt_correction_T_max  0.8958
_exptl_absorpt_correction_T_min  0.782875452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS - Bruker'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_density_method    none
_exptl_crystal_description       rhomb
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.368
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.021(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0210
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0273P)^2^+0.4654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0554
_refine_ls_wR_factor_ref         0.0555
_reflns_number_gt                3361
_reflns_number_total             3391
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02500_si_001.cif
_cod_data_source_block           MDI034
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4035938
_chemical_formula_friedif_mrl    234