A Novel and Efficient Synthesis of a Highly Active Analogue of clasto-Lactacystin β-Lactone
François Soucy; Louis Grenier; Mark L. Behnke; Antonia T. Destree; Teresa A. McCormack; Julian Adams; Louis Plamondon; Journal of the American Chemical Society 121 (1999) 9967–9976; doi:10.1021/ja991175f

data_4116571
_publ_section_title
;
 A Novel and Efficient Synthesis of a Highly Active Analogue of
 clasto-Lactacystin \b-Lactone
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9967
_journal_page_last               9976
_journal_paper_doi               10.1021/ja991175f
_journal_volume                  121
_journal_year                    1999
_chemical_formula_sum            'C13 H23 N O5'
_chemical_formula_weight         273.32
_chemical_name_common            'g-lactam 4'
_chemical_name_systematic
; 
3S-Hydroxy-2R-(1S-hydroxy-2-methyl-propyl)-4R-n-propyl-5- 
oxo-pyrrolidine-2-carboxylic acid methyl ester
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   10.536(2)
_cell_length_b                   20.451(4)
_cell_length_c                   27.557(6)
_cell_measurement_reflns_used    153
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      12.54
_cell_measurement_theta_min      2.07
_cell_volume                     5938(2)
_computing_cell_refinement       'SMART (Bruker, V4.050, 1995)'
_computing_data_collection       'ASTRO (Bruker, V4.050, 1995)'
_computing_data_reduction        'SAINT (Bruker, V5.A06, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998, ver 5.10)'
_computing_publication_material  'CIFTAB (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_method       '\w, 0.3 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_sigmaI/netI    0.0791
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            25661
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         1.48
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       needles
_exptl_crystal_F_000             2368
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.817
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     685
_refine_ls_number_reflns         7779
_refine_ls_number_restraints     456
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0736
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0808P)^2^+11.6062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1714
_refine_ls_wR_factor_ref         0.1957
_reflns_number_gt                5316
_reflns_number_total             7779
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja991175f.cif
_cod_data_source_block           g-lactam_4
_cod_database_code               4116571