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_7154612
_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         'C27 H28 N1 O8 P1 S1'
_chemical_formula_sum            'C27 H28 N O8 P S'
_chemical_formula_weight         557.56
_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
_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                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   11.8008(5)
_cell_length_b                   14.3566(8)
_cell_length_c                   16.6799(11)
_cell_measurement_reflns_used    2333
_cell_measurement_temperature    293
_cell_measurement_theta_max      21
_cell_measurement_theta_min      3
_cell_volume                     2825.9(3)
_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 0.966
_diffrn_measured_fraction_theta_max 0.887
_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  0.054
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12345
_diffrn_reflns_theta_full        25.271
_diffrn_reflns_theta_max         29.385
_diffrn_reflns_theta_min         2.824
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.133
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.48
_refine_ls_abs_structure_details 'Flack (1983), 3579 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.17(16)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1191
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         2690
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1498
_refine_ls_R_factor_gt           0.0788
_refine_ls_shift/su_max          0.0001801
_refine_ls_shift/su_mean         0.0000158
_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: 
 8.17 -2.54 7.30 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0806
_refine_ls_wR_factor_gt          0.0595
_refine_ls_wR_factor_ref         0.0536
_reflns_limit_h_max              15
_reflns_limit_h_min              -16
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                3417
_reflns_number_total             6417
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.23
_oxford_diffrn_Wilson_scale      1.59
_oxford_refine_ls_r_factor_ref   0.0562
_oxford_refine_ls_scale          0.958(3)
_oxford_reflns_number_all        6398
_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_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C27 H28 N1 O8 P1 S1'
_cod_database_code               7154612
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) H   ( 252,X'S) H   ( 253,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  38,X'S) H   ( 382,X'S) H   ( 381,X'S) H   ( 383,X'S) 
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 = C(17) TO C(18) 
U(IJ)'S  0.0, 0.010000 = C(18) TO C(19) 
U(IJ)'S  0.0, 0.010000 = C(19) TO C(20) 
U(IJ)'S  0.0, 0.010000 = C(17) TO C(22) 
U(IJ)'S  0.0, 0.010000 = C(18) TO C(23) 
U(IJ)'S  0.0, 0.010000 = C(20) TO C(21) 
END                                                                             
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