Stereoselective Synthesis of C-Substituted Morpholine Derivatives using Reductive Etherification Reaction: Total Synthesis of Chelonin C
Santosh J. Gharpure; J. V. K. Prasad; Journal of Organic Chemistry 76 (2011) 10325–10331; doi:10.1021/jo201975b

data_4026799
_publ_section_title
;
 Stereoselective Synthesis of C-Substituted Morpholine Derivatives using
 Reductive Etherification Reaction: Total Synthesis of Chelonin C
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10325
_journal_page_last               10331
_journal_paper_doi               10.1021/jo201975b
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C14 H19 N O5 S'
_chemical_formula_sum            'C14 H19 N O5 S'
_chemical_formula_weight         313.36
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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                   9.6498(5)
_cell_length_b                   9.7688(4)
_cell_length_c                   16.9162(8)
_cell_measurement_reflns_used    4281
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.70
_cell_measurement_theta_min      2.43
_cell_volume                     1594.64(13)
_computing_cell_refinement       'APEXII/SAINT, Bruker,2004'
_computing_data_collection       'APEXII, Bruker,2004'
_computing_data_reduction        'SAINT PLUS/XPREP, Bruker,2004'
_computing_molecular_graphics    'ORTEP-3   (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97  (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97  (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97  (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11486
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.9527
_exptl_absorpt_correction_T_min  0.9202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS(Bruker,2004)
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       Block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0513P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                2967
_reflns_number_total             3810
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201975b_si_002.cif
_cod_data_source_block           new
_cod_database_code               4026799