Synthesis, Characterization, and Coupling Reactions of Six-Membered Cyclic P-Chiral Ammonium Phosphonite-Boranes; Reactive H-Phosphinate Equivalents for the Stereoselective Synthesis of Glycomimetics
Angélique Ferry; Xavier Guinchard; Pascal Retailleau; David Crich; Journal of the American Chemical Society 134 (2012) 12289–12301; doi:10.1021/ja305104b

data_4118360
_publ_contact_author_address
;Centre de Recherches de Gif
Institut de Chimie des Substances Naturelles-CNRS
1 avenue de la Terrasse
91198 Gif sur Yvette
France
;
_publ_contact_author_email       xavier.guinchard@icsn.cnrs-gif.fr
_publ_contact_author_fax         +33169077247
_publ_contact_author_name        'Guinchard, Xavier'
_publ_contact_author_phone       +33169823011
_publ_section_title
;
 Synthesis, Characterization, and Coupling Reactions of Six-Membered
 Cyclic P-Chiral Ammonium Phosphonite-Boranes; Reactive H-Phosphinate
 Equivalents for the Stereoselective Synthesis of Glycomimetics
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12289
_journal_page_last               12301
_journal_paper_doi               10.1021/ja305104b
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H29 O9 P'
_chemical_formula_sum            'C24 H29 O9 P'
_chemical_formula_weight         492.44
_chemical_name_systematic
; 
((2S,3S,4S,5S,6R)-3-acetoxy-4,5-bis(benzyloxy)-2-methoxy-2-oxido-1,2-
oxaphosphinan-6-yl)methyl acetate
;
_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
_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                   5.28510(10)
_cell_length_b                   11.5055(3)
_cell_length_c                   42.054(3)
_cell_measurement_reflns_used    1728
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.1
_cell_measurement_theta_min      6.5
_cell_volume                     2557.2(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_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_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details
;
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 720.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 18
               Slice: 20.0000 - 110.0000
         Image width: 5.0000
            Exp time: 720.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 180.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 15
               Slice: 22.0000 - 99.0000
         Image width: 5.0000
            Exp time: 720.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 270.0000
                 XTD: 127.4000
              2theta: 0.0000

;
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.003692
_diffrn_orient_matrix_UB_12      0.083531
_diffrn_orient_matrix_UB_13      0.006556
_diffrn_orient_matrix_UB_21      -0.003467
_diffrn_orient_matrix_UB_22      0.023933
_diffrn_orient_matrix_UB_23      -0.022856
_diffrn_orient_matrix_UB_31      -0.189152
_diffrn_orient_matrix_UB_32      -0.002069
_diffrn_orient_matrix_UB_33      0.000291
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            11122
_diffrn_reflns_theta_full        65.07
_diffrn_reflns_theta_max         65.07
_diffrn_reflns_theta_min         6.52
_exptl_absorpt_coefficient_mu    1.375
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       needdle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 1657 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_coef       0.00178(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4131
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0000P)^2^+3.2117P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1289
_reflns_number_gt                3079
_reflns_number_total             4132
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja305104b_si_002_3.cif
_cod_data_source_block           8g\b
_cod_database_code               4118360