A general and concise asymmetric synthesis of sphingosine, safingol and phytosphingosines via tethered aminohydroxylation.
Kumar, Pradeep; Dubey, Abhishek; Puranik, Vedavati G.; Organic & biomolecular chemistry 8 (2010) 5074–5086; doi:10.1039/c0ob00117a

data_7153434
_publ_section_title
;
 A general and concise asymmetric synthesis of sphingosine, safingol and
 phytosphingosines via tethered aminohydroxylation.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5074
_journal_page_last               5086
_journal_paper_doi               10.1039/c0ob00117a
_journal_volume                  8
_journal_year                    2010
_chemical_formula_moiety         'C18 H35 N O2'
_chemical_formula_sum            'C18 H35 N O2'
_chemical_formula_weight         297.47
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.207(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.9598(5)
_cell_length_b                   5.2424(4)
_cell_length_c                   30.618(2)
_cell_measurement_reflns_used    1885
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.086
_cell_measurement_theta_min      2.668
_cell_volume                     954.04(12)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    'SHELXTL, PyMOL and PLATON'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'Omega Scan'
_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  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            7910
_diffrn_reflns_theta_full        23.50
_diffrn_reflns_theta_max         23.50
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_correction_T_min  0.9825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.036
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.182
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0732
_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^)+(0.0774P)^2^+0.1004P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1667
_refine_ls_wR_factor_ref         0.1788
_reflns_number_gt                2120
_reflns_number_total             2808
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00117a.txt
_cod_data_source_block           C18H35NO2compound27
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        954.04(13)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7153434