Asymmetric Syntheses of Methyl N,O-Diacetyl-d-3-epi-daunosaminide and Methyl N,O-Diacetyl-d-ristosaminide
Kristína Csatayová; Stephen G. Davies; J. Gair Ford; James A. Lee; Paul M. Roberts; James E. Thomson; Journal of Organic Chemistry 78 (2013) 12397–12408; doi:10.1021/jo4020563

data_4028848
_publ_contact_author             'Stephen G. Davies'
_publ_contact_author_email       steve.davies@chem.ox.ac.uk
_publ_contact_author_fax         '+44 1865 275633'
_publ_contact_author_phone       '+44 1865 275695'
_publ_section_title
;
 Asymmetric Syntheses of Methyl N,O-Diacetyl-d-3-epi-daunosaminide and
 Methyl N,O-Diacetyl-d-ristosaminide
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12397
_journal_page_last               12408
_journal_paper_doi               10.1021/jo4020563
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H26.64 N1 O2'
_chemical_formula_sum            'C22 H26.64 N O2'
_chemical_formula_weight         337.10
_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                 98.519(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8277(3)
_cell_length_b                   7.6317(2)
_cell_length_c                   14.3944(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     959.06(5)
_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 0.986
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8846
_diffrn_reflns_theta_full        74.428
_diffrn_reflns_theta_max         76.730
_diffrn_reflns_theta_min         3.104
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_T_max  0.9383
_exptl_absorpt_correction_T_min  0.9329
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       block
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_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.12
_refine_diff_density_min         -0.15
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.08(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9969
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         8846
_refine_ls_number_restraints     730
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.0114716
_refine_ls_shift/su_mean         0.0006860
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.07P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0970
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0970
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                8273
_reflns_number_total             2157
_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   0.0397
_oxford_refine_ls_scale          10.8(3)
_oxford_reflns_number_all        8846
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            jo4020563_si_001_2.cif
_cod_data_source_block           25
_cod_original_cell_volume        959.05(5)
_cod_original_formula_sum        'C22 H26.64 N1 O2'
_cod_database_code               4028848