Asymmetric Syntheses of APTO and AETD: the β-Amino Acid Fragments within Microsclerodermins C, D, and E
Stephen G. Davies; Ai M. Fletcher; Emma M. Foster; James A. Lee; Paul M. Roberts; James E. Thomson; Journal of Organic Chemistry 78 (2013) 2500–2510; doi:10.1021/jo302731m

data_4028050
_publ_contact_author             'Stephen G. Davies'
_publ_contact_author_email       steve.davies@chem.ox.ac.uk
_publ_contact_author_fax         '+44 1865 275633'
_publ_contact_author_phone       '+44 1865 275695'
_publ_section_title
;
 Asymmetric Syntheses of APTO and AETD: the \b-Amino Acid Fragments within
 Microsclerodermins C, D, and E
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2500
_journal_page_last               2510
_journal_paper_doi               10.1021/jo302731m
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H39 N1 O8'
_chemical_formula_sum            'C27 H39 N O8'
_chemical_formula_weight         505.61
_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   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3465(3)
_cell_length_b                   20.9082(13)
_cell_length_c                   25.0180(15)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2796.7(3)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.119
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            34106
_diffrn_reflns_theta_full        74.618
_diffrn_reflns_theta_max         77.728
_diffrn_reflns_theta_min         3.533
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_T_max  0.9506
_exptl_absorpt_correction_T_min  0.9370
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.46
_refine_ls_abs_structure_details 'Flack (1983), 2448 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.11(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0630
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5364
_refine_ls_number_restraints     98
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0999
_refine_ls_shift/su_max          0.0001506
_refine_ls_shift/su_mean         0.0000114
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.10P)^2^ + 4.34P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2588
_refine_ls_wR_factor_gt          0.2430
_refine_ls_wR_factor_ref         0.2588
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              31
_reflns_limit_l_min              0
_reflns_number_gt                3837
_reflns_number_total             5836
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.37
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.1233
_oxford_refine_ls_scale          5.7(3)
_oxford_reflns_number_all        5364
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            jo302731m_si_001_1.cif
_cod_data_source_block           45
_cod_original_formula_sum        'C27 H39 N1 O8'
_cod_database_code               4028050