Total Synthesis and Absolute Configuration of the Natural Amino Acid Tetrahydrolathyrine
Meryem Benohoud; Loïc Leman; Silvia H. Cardoso; Pascal Retailleau; Philippe Dauban; Josiane Thierry; Robert H. Dodd; Journal of Organic Chemistry 74 (2009) 5331–5336; doi:10.1021/jo900800x

data_4024688
_publ_contact_author_address
;Institut de Chimie des Substances Naturelles, UPR 2301,
Centre National de la Recherche Scientifique,
 b\^at. 27, 1 av. de la Terrasse, F-91198 Gif-sur-Yvette, France

;
_publ_contact_author_email       dodd@icsn.cnrs-gif.fr
_publ_contact_author_fax         '33 1 69077247'
_publ_contact_author_name        'DODD, Robert H.'
_publ_contact_author_phone       '33 1 69824594'
_publ_section_title
;
Total Synthesis and Absolute Configuration of the Natural Amino Acid
Tetrahydrolathyrine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5331
_journal_page_last               5336
_journal_paper_doi               10.1021/jo900800x
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C16 H20 N4 O4'
_chemical_formula_sum            'C16 H20 N4 O4'
_chemical_formula_weight         332.36
_chemical_name_systematic
; 
 benzyl (S)-6-(((S)-2-oxooxazolidin-4-yl)methyl)-1,4,5,6-
 tetrahydropyrimidin-2-ylcarbamate 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             18-02-09
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.828(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.886(2)
_cell_length_b                   12.116(5)
_cell_length_c                   23.233(5)
_cell_measurement_reflns_used    1315
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.782
_cell_measurement_theta_min      0.998
_cell_volume                     1651.0(10)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0786
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4204
_diffrn_reflns_theta_full        19.76
_diffrn_reflns_theta_max         19.76
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'flat parallelepiped'
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         1515
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0524
_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^)+(0.0705P)^2^+0.2030P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                1011
_reflns_number_total             1515
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900800x_si_002.cif
_cod_data_source_block           mb210-b
_cod_original_sg_symbol_H-M      P21
_cod_database_code               4024688