Total Synthesis of (-)-4,8,10-Tridesmethyl Telithromycin
Venkata Velvadapu; Tapas Paul; Bharat Wagh; Ian Glassford; Charles DeBrosse; Rodrigo B. Andrade; Journal of Organic Chemistry 76 (2011) 7516–7527; doi:10.1021/jo201319b

data_4026587
_publ_section_title
;
 Total Synthesis of (-)-4,8,10-Tridesmethyl Telithromycin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7516
_journal_page_last               7527
_journal_paper_doi               10.1021/jo201319b
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C31 H60 O7 Si2'
_chemical_formula_weight         600.97
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.760(5)
_cell_angle_beta                 79.926(5)
_cell_angle_gamma                64.920(5)
_cell_formula_units_Z            4
_cell_length_a                   14.5401(15)
_cell_length_b                   15.8885(15)
_cell_length_c                   18.4527(15)
_cell_measurement_temperature    143(1)
_cell_volume                     3800.8(6)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.896
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31750
_diffrn_reflns_theta_full        22.55
_diffrn_reflns_theta_max         22.55
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.050
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.895
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.18(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1443
_refine_ls_number_reflns         26883
_refine_ls_number_restraints     504
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0770
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1165P)^2^+4.9260P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1958
_refine_ls_wR_factor_ref         0.2169
_reflns_number_gt                23395
_reflns_number_total             26883
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201319b_si_002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 1 '
_cod_database_code               4026587