Chiral Iminoesters Derived fromd-Glyceraldehyde in [3 + 2] Cycloaddition Reactions. Asymmetric Synthesis of a Key Intermediate in the Synthesis of Neuramidinase Inhibitors
José A. Gálvez; María D. Díaz-de-Villegas; Miriam Alías; Ramón Badorrey; Journal of Organic Chemistry 78 (2013) 11404–11413; doi:10.1021/jo401967a

data_4028757
_publ_section_title
;
 Chiral Iminoesters Derived fromd-Glyceraldehyde in [3 + 2] Cycloaddition
 Reactions. Asymmetric Synthesis of a Key Intermediate in the Synthesis of
 Neuramidinase Inhibitors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11404
_journal_page_last               11413
_journal_paper_doi               10.1021/jo401967a
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C16 H19 N O7 S'
_chemical_formula_sum            'C16 H19 N O7 S'
_chemical_formula_weight         369.38
_chemical_name_systematic
; 
(2S,3aS,6S,6aR)-methyl 6-(hydroxymethyl)-4-oxo-1-tosylhexahydro
-1H-furo[3,4-b]pyrrole-2-carboxylate 
;
_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            4
_cell_length_a                   7.0511(2)
_cell_length_b                   9.8605(2)
_cell_length_c                   24.4965(6)
_cell_measurement_reflns_used    3416
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8447
_cell_measurement_theta_min      2.8830
_cell_volume                     1703.18(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.909
_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  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12809
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         28.91
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0417P)^2^+0.3857P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                3237
_reflns_number_total             3844
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401967a_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4028757