Diastereoselective Synthesis of the Leu-Pro Type Phosphinyl Dipeptide Isostere
Takehiro Yamagishi; Naoko Tashiro; Tsutomu Yokomatsu; Journal of Organic Chemistry 76 (2011) 5472–5476; doi:10.1021/jo200669r

data_4026421
_publ_contact_author_address
;
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences,
1432-1 Horinouchi Hachioji, Tokyo, 192-0392, Japan
;
_publ_section_title
;
 Diastereoselective Synthesis of the Leu-Pro Type Phosphinyl Dipeptide
 Isostere
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5472
_journal_page_last               5476
_journal_paper_doi               10.1021/jo200669r
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C32 H55 N2 O6 P S'
_chemical_formula_sum            'C32 H55 N2 O6 P S'
_chemical_formula_weight         626.81
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             '26 December 08'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.496(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.344(2)
_cell_length_b                   16.574(3)
_cell_length_c                   15.857(2)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.27
_cell_volume                     3490.9(9)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            39483
_diffrn_reflns_theta_full        27.69
_diffrn_reflns_theta_max         27.69
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.9528
_exptl_absorpt_correction_T_min  0.9328
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         8083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+1.5940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                6644
_reflns_number_total             8083
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200669r_si_001.cif
_cod_data_source_block           mas3-30-pi
_cod_original_cell_volume        3490.8(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4026421