d-Glucosamine as a novel chiral auxiliary for the stereoselective synthesis of P-stereogenic phosphine oxides.
D'Onofrio, A; Copey, L.; Jean-Gérard, L; Goux-Henry, C; Pilet, G.; Andrioletti, B.; Framery, E.; Organic & biomolecular chemistry 13 (2015) 9029–9034; doi:10.1039/c5ob01323b

data_7154611
_publ_section_title
;
 d-Glucosamine as a novel chiral auxiliary for the stereoselective
 synthesis of P-stereogenic phosphine oxides.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9029
_journal_page_last               9034
_journal_paper_doi               10.1039/c5ob01323b
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H40 N1 O9 P1 S1'
_chemical_formula_sum            'C31 H40 N O9 P S'
_chemical_formula_weight         633.70
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2015-05-11 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 105.023(5)
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   10.2628(5)
_cell_length_b                   8.9164(4)
_cell_length_c                   18.5939(9)
_cell_measurement_reflns_used    3763
_cell_measurement_temperature    293
_cell_measurement_theta_max      24
_cell_measurement_theta_min      3
_cell_volume                     1643.32(14)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_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    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10873
_diffrn_reflns_theta_full        25.193
_diffrn_reflns_theta_max         29.295
_diffrn_reflns_theta_min         3.082
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.515
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.142
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.23
_refine_ls_abs_structure_details 'Flack (1983), 2243 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.08(8)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1530
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         3953
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.0002826
_refine_ls_shift/su_mean         0.0000321
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 3.31 -1.39 2.54 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0546
_refine_ls_wR_factor_gt          0.0436
_refine_ls_wR_factor_ref         0.0406
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              9
_reflns_limit_k_min              -12
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                4677
_reflns_number_total             6292
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0409
_oxford_refine_ls_scale          1.859(3)
_oxford_reflns_number_all        6279
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            c5ob01323b2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7154610--7154612.cif.'
_cod_original_cell_volume        1643.33(14)
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C31 H40 N1 O9 P1 S1'
_cod_database_code               7154611
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
U(IJ)'S  0.0, 0.010000 = O(40) TO C(41) 
U(IJ)'S  0.0, 0.010000 = C(41) TO C(42) 
END                                                                             
;