A Robust Platform for the Synthesis of New Tetracycline Antibiotics
Cuixiang Sun; Qiu Wang; Jason D. Brubaker; Peter M. Wright; Christian D. Lerner; Kevin Noson; Mark Charest; Dionicio R. Siegel; Yi-Ming Wang; Andrew G. Myers; Journal of the American Chemical Society 130 (2008) 17913–17927; doi:10.1021/ja806629e

data_4108939
_publ_section_title
;
 A Robust Platform for the Synthesis of New Tetracycline Antibiotics
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17913
_journal_page_last               17927
_journal_paper_doi               10.1021/ja806629e
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_compound_source        'chemical synthesis'
_chemical_formula_iupac          'C26 H34 N2 O5 Si'
_chemical_formula_moiety         'C26 H34 N2 O5 Si'
_chemical_formula_structural     'C26 H34 N2 O5 Si'
_chemical_formula_sum            'C26 H34 N2 O5 Si'
_chemical_formula_weight         482.64
_chemical_name_common            drsenone
_chemical_name_systematic
; 
(4a<i>S</i>,8a<i>S</i>,9<i>S</i>)-3-(Benzyloxy)-4a-(<i>tert</i>-
butyldimethylsilyloxy)-9-(dimethylamino)-8a,9-
dihydronaphtho[2,3-<i>d</i>]isoxazole-4,5(4a<i>H</i>,8<i>H</i>)-dione
;
_space_group_IT_number           19
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7457(7)
_cell_length_b                   9.5756(7)
_cell_length_c                   31.598(2)
_cell_measurement_reflns_used    4045
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.69
_cell_measurement_theta_min      2.42
_cell_volume                     2646.2(3)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_collection       'SMART V5.625(NT) (Bruker AXS, 2001a)'
_computing_data_reduction
;
SAINT V7.34A (Bruker AXS, 2006), SADABS (Bruker AXS, 2004)
;
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001b)'
_computing_publication_material  'SHELXTL v6.12 (Bruker AXS, 2001b)'
_computing_structure_refinement  'SHELXTL v6.12 (Bruker AXS, 2001b)'
_computing_structure_solution    'SHELXTL v6.12 (Bruker AXS, 2001b)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       '\w scans, 997 0.3\% rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0666
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            13822
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2004)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       Block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         5935
_refine_ls_number_restraints     180
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.0707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                4149
_reflns_number_total             5935
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja806629e_si_003.cif
_cod_data_source_block           agm078
_cod_original_cell_volume        2646.2(4)
_cod_database_code               4108939