Single-Step Ugi Multicomponent Reaction for the Synthesis of Phosphopeptidomimetics
Andrea F. G. Gargano; Stefanie Buchinger; Michal Kohout; Wolfgang Lindner; Michael Lämmerhofer; Journal of Organic Chemistry 78 (2013) 10077–10087; doi:10.1021/jo401372x

data_4028658
_publ_contact_author_address
;
Institute of Pharmaceutical Sciences
University of T\"ubingen
Auf der Morgenstelle 8
72076 T\"ubingen, Germany
;
_publ_contact_author_email       michael.laemmerhofer@uni-tuebingen.de
_publ_contact_author_fax         '+49 7071 29 4565'
_publ_contact_author_name        'Michael Laemmerhofer'
_publ_contact_author_phone       '+49 7071 29 78793'
_publ_section_title
;
 Single-Step Ugi Multicomponent Reaction for the Synthesis of
 Phosphopeptidomimetics
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10077
_journal_page_last               10087
_journal_paper_doi               10.1021/jo401372x
_journal_volume                  78
_journal_year                    2013
_chemical_compound_source
'University Of Vienna, Department of Analytical Chemistry'
_chemical_formula_moiety         'C20 H27 N2 O4 P, 2(C2 H6 O S)'
_chemical_formula_sum            'C24 H39 N2 O6 P S2'
_chemical_formula_weight         546.66
_chemical_name_systematic
;      
Methylhydrogen[2-({2-[(2,6-dimethylphenyl)amino]-2-oxo-1-phenylethyl}amino)
propane-2-yl]phosphonate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                108.637(5)
_cell_angle_beta                 95.801(6)
_cell_angle_gamma                95.605(4)
_cell_formula_units_Z            2
_cell_length_a                   9.373(3)
_cell_length_b                   12.019(4)
_cell_length_c                   13.078(4)
_cell_measurement_reflns_used    3783
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.6
_cell_measurement_theta_min      3.0
_cell_volume                     1375.6(8)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_molecular_graphics
;
Images generated using CrystalMaker: a crystal and molecular 
structures program for Mac and Windows. CrystalMaker Software Ltd, 
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_pressure         101.325
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_radiation_collimation    'Confocal mirrors, VHF Varimax '
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0820
_diffrn_reflns_av_unetI/netI     0.0955
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20014
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.969
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_type              'FR-E+ SuperBright '
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method DMSO
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0691
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+0.7477P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1320
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4025
_reflns_number_total             5617
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo401372x_si_002.cif
_cod_data_source_block           2012scas0005
_cod_original_cell_volume        1375.7(7)
_cod_database_code               4028658
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.997
_shelxl_version_number           2012-9
_shelx_res_checksum              67514