Diastereoselective Synthesis of 2-Amino-4-phosphonobutanoic Acids by Electrophilic Substitution and Tin-Peterson Olefination of Bis-lactim Ethers Derived from cyclo-[L-AP4-D-Val]
María C. Fernández; Aniana Díaz; Juan J. Guillín; Olga Blanco; María Ruiz; Vicente Ojea; Journal of Organic Chemistry 71 (2006) 6958–6974; doi:10.1021/jo061072x

data_4021945
_publ_contact_author_address
;
  Dna. Ana I. Balana
  Servizos Xerais de Apoio 'a Investigaci\'on.
  Universidade da Coru\~na.
  Castro de Elvi\~na, sn. 
  15.192, A Coru\~na, Spain
  
;
_publ_contact_author_email       sxairx@udc.es
_publ_contact_author_fax         '+34 976 167068'
_publ_contact_author_name        'Ana I. Balana'
_publ_contact_author_phone       '+34 981 167000 ext 2630'
_publ_section_title
;
 Diastereoselective Synthesis of 2-Amino-4-phosphonobutanoic Acids
 by Electrophilic Substitution and Tin-Peterson Olefination of Bis-lactim
 Ethers Derived from cyclo-[L-AP4-D-Val]
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6958
_journal_page_last               6974
_journal_paper_doi               10.1021/jo061072x
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H28 N O5 P, 0.5(H2 O)'
_chemical_formula_sum            'C18 H29 N O5.5 P'
_chemical_formula_weight         378.39
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_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                 101.189(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.3035(16)
_cell_length_b                   10.3641(11)
_cell_length_c                   14.1931(15)
_cell_measurement_reflns_used    2969
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.373
_cell_measurement_theta_min      2.388
_cell_volume                     2208.3(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  '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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7785
_diffrn_reflns_theta_full        28.12
_diffrn_reflns_theta_max         28.12
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.9491
_exptl_absorpt_correction_T_min  0.9421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; SADABS: Area-Detector Absorption Correction. Bruker-AXS 
  within SAINT+ package, v. 6.22 (2001).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.12(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    calc
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5036
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0643P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1168
_reflns_number_gt                3396
_reflns_number_total             5036
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061072xsi20060524_021005.cif
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C18 H29 N O5.50 P'
_cod_database_code               4021945