An Efficient, Stereocontrolled Synthesis of a Potent Omuralide-Salinosporin Hybrid for Selective Proteasome Inhibition
Leleti Rajender Reddy; Jean-François Fournier; B. V. Subba Reddy; E. J. Corey; Journal of the American Chemical Society 127 (2005) 8974–8976; doi:10.1021/ja052376o

data_4111794
_publ_section_title
;
 An Efficient, Stereocontrolled Synthesis of a Potent
 Omuralide-Salinosporin Hybrid for Selective Proteasome Inhibition
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8974
_journal_page_last               8976
_journal_paper_doi               10.1021/ja052376o
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C26 H41 N O6 Si'
_chemical_formula_weight         491.69
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.607(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.224(2)
_cell_length_b                   8.8408(15)
_cell_length_c                   13.842(2)
_cell_measurement_temperature    193(2)
_cell_volume                     1390.8(4)
_computing_cell_refinement       'SMART (BRUKER, V5.625, 2001)'
_computing_data_collection       'ASTRO (BRUKER, V5.007, 1997)'
_computing_data_reduction        'SAINT (BRUKER, V6.22, 2001)'
_computing_molecular_graphics    'SHELXTL (BRUKER, 2000, V6.1)'
_computing_publication_material  'XCIF (Sheldrick and BRUKER, 1997, V5.1)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       '\w, 0.3 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9123
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         1.58
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_meas      0
_exptl_crystal_description       chunk
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.285
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5928
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0759
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0782P)^2^+1.2164P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1794
_refine_ls_wR_factor_ref         0.1824
_reflns_number_gt                5571
_reflns_number_total             5928
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja052376osi20050412_123618.cif
_cod_data_source_block           ejc82t
_cod_original_cell_volume        1390.9(4)
_cod_database_code               4111794