Synthesis of α, β-unsaturated γ-amino esters with unprecedented high (E)-stereoselectivity and their conformational analysis in peptides.
Mali, Sachitanand M.; Bandyopadhyay, Anupam; Jadhav, Sandip V.; Kumar, Mothukuri Ganesh; Gopi, Hosahudya N.; Organic & biomolecular chemistry 9 (2011) 6566–6574; doi:10.1039/c1ob05732d

data_7151991
_publ_section_title
;
 Synthesis of \a, \b-unsaturated \g-amino esters with unprecedented
 high (E)-stereoselectivity and their conformational analysis in
 peptides.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6566
_journal_page_last               6574
_journal_paper_doi               10.1039/c1ob05732d
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_compound_source        synthesis
_chemical_formula_sum            'C17 H30 N2 O5'
_chemical_formula_weight         342.43
_chemical_name_common            'alpha gamma mixed peptide'
_chemical_name_systematic
;(S,E)-ethyl 4-((S)-2-(tert-butoxycarbonylamino)propanamido)
-5-methylhex-2-enoate
Chemical Formula: C17H30N2O5
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.064(5)
_cell_angle_beta                 70.670(4)
_cell_angle_gamma                73.874(5)
_cell_formula_units_Z            6
_cell_length_a                   13.3376(19)
_cell_length_b                   14.030(2)
_cell_length_c                   17.956(3)
_cell_measurement_temperature    100(2)
_cell_volume                     3039.6(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_pressure         101.325
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_sigmaI/netI    0.1482
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            54826
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.51
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Graphite monochromator'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'square block'
_exptl_crystal_F_000             1116
_exptl_crystal_recrystallization_method EtOAc/hexane
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1339
_refine_ls_number_reflns         25408
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1817
_refine_ls_R_factor_gt           0.0881
_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^)+(0.1203P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1946
_refine_ls_wR_factor_ref         0.2449
_reflns_number_gt                12742
_reflns_number_total             25408
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05732d.txt
_cod_data_source_block           hngbadgv
_cod_original_cell_volume        3039.6(7)
_cod_database_code               7151991