Diastereoselective synthesis of alpha,beta'-disubstituted aminomethyl(2-carboxyethyl)phosphinates as phosphinyl dipeptide isosteres.
Yamagishi, Takehiro; Ichikawa, Hiroyuki; Haruki, Terumitsu; Yokomatsu, Tsutomu; Organic letters 10 (2008) 4347–4350; doi:10.1021/ol801743d

data_1504888
_publ_section_title
;
 Diastereoselective synthesis of alpha,beta'-disubstituted
 aminomethyl(2-carboxyethyl)phosphinates as phosphinyl dipeptide
 isosteres.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4347
_journal_page_last               4350
_journal_paper_doi               10.1021/ol801743d
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C24 H34 N O6 P S'
_chemical_formula_sum            'C24 H34 N O6 P S'
_chemical_formula_weight         495.55
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             '4 June 08'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.979(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.3175(17)
_cell_length_b                   10.3715(12)
_cell_length_c                   17.180(2)
_cell_measurement_reflns_used    2523
_cell_measurement_temperature    90
_cell_measurement_theta_max      26.24
_cell_measurement_theta_min      2.37
_cell_volume                     2550.8(5)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'multilayer confocal mirror'
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13901
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.9644
_exptl_absorpt_correction_T_min  0.9580
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0404P)^2^+0.9193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1080
_reflns_number_gt                4142
_reflns_number_total             5765
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801743d_si_005.cif
_cod_data_source_block           IHI_2_35
_cod_original_cell_volume        2550.7(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1504888