Asymmetric syntheses of (-)-3-epi-Fagomine, (2R,3S,4R)-dihydroxypipecolic acid, and several polyhydroxylated homopipecolic acids.
Csatayová, Kristína; Davies, Stephen G.; Fletcher, Ai M.; Ford, J. Gair; Klauber, David J.; Roberts, Paul M.; Thomson, James E.; The Journal of organic chemistry 79 (2014) 10932–10944; doi:10.1021/jo501952t

data_4030114
_publ_section_title
;
 Asymmetric syntheses of (-)-3-epi-Fagomine, (2R,3S,4R)-dihydroxypipecolic
 acid, and several polyhydroxylated homopipecolic acids.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10932
_journal_page_last               10944
_journal_paper_doi               10.1021/jo501952t
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C7 H15 N1 O5'
_chemical_formula_sum            'C7 H15 N O5'
_chemical_formula_weight         193.20
_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
_cell_angle_alpha                90
_cell_angle_beta                 89.7378(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.16990(10)
_cell_length_b                   7.3333(2)
_cell_length_c                   11.1791(2)
_cell_measurement_reflns_used    3238
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     423.822(16)
_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 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4290
_diffrn_reflns_theta_full        74.181
_diffrn_reflns_theta_max         76.475
_diffrn_reflns_theta_min         3.954
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.101
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.17
_refine_ls_abs_structure_details 'Flack (1983), 613 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.0004499
_refine_ls_shift/su_mean         0.0001157
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 0.10P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0832
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0832
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              7
_reflns_limit_k_min              -9
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1163
_reflns_number_total             1567
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.26
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0328
_oxford_refine_ls_scale          17.9(20)
_oxford_reflns_number_all        1166
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            jo501952t_si_001.cif
_cod_data_source_block           21.H2O
_cod_depositor_comments
'Adding full bibliography for 4030114--4030119.cif.'
_cod_original_formula_sum        'C7 H15 N1 O5'
_cod_database_code               4030114
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   4,X'S) H   (  41,X'S) H   (  42,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE N   (   6,X'S) H   (  62,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE O   (  11,X'S) H   ( 111,X'S) 
RIDE O   (  12,X'S) H   ( 121,X'S) 
RIDE O   (  13,X'S) H   ( 131,X'S) H   ( 132,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) 
END                                                                             
;