A stereoselective synthesis of 6,6,6-trifluoro-L-daunosamine and 6,6,6-trifluoro-L-acosamine.
Hayman, Colin M.; Larsen, David S.; Simpson, Jim; Bailey, Karl B.; Gill, Gurmit Singh; Organic & biomolecular chemistry 4 (2006) 2794–2800; doi:10.1039/b606055b

data_7151257
_publ_section_title
;
 A stereoselective synthesis of 6,6,6-trifluoro-L-daunosamine and
 6,6,6-trifluoro-L-acosamine.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2794
_journal_page_last               2800
_journal_paper_doi               10.1039/b606055b
_journal_volume                  4
_journal_year                    2006
_chemical_absolute_configuration rm
_chemical_formula_sum            'C18 H21 F6 N O4'
_chemical_formula_weight         429.36
_chemical_name_systematic
;
N-(6-ethoxy-3-hydroxy-2-(trifluoromethyl)-tetrahydro-2H-pyran-4-yl)-
2,2,2-trifluoro-N-(1-phenylethyl)acetamide
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.345(3)
_cell_angle_beta                 98.080(3)
_cell_angle_gamma                103.188(3)
_cell_formula_units_Z            2
_cell_length_a                   9.499(2)
_cell_length_b                   10.601(3)
_cell_length_c                   11.958(3)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      8.64
_cell_volume                     1039.9(5)
_computing_cell_refinement       'SAINT (Bruker 1999)'
_computing_data_collection       'SMART (Bruker 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) & PLATON (Spek 1995)
;
_computing_publication_material
;
SHELXL-97 & enCIFER V1.1 (Allen et al., 2004)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, 1997) & TITAN2000 (Hunter & Simpson, 1999)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Bruker CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13093
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.68
_diffrn_reflns_theta_min         2.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Friedel pairs were averaged'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         4459
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0577P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                3981
_reflns_number_total             4459
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b606055b.txt
_cod_data_source_block           feda
_cod_original_cell_volume        1039.9(4)
_cod_database_code               7151257