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_4028847
_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         'C11 H19 N1 O5'
_chemical_formula_sum            'C11 H19 N O5'
_chemical_formula_weight         245.28
_space_group_IT_number           79
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      79
_symmetry_space_group_name_Hall  'I 4'
_symmetry_space_group_name_H-M   'I 4'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.9621(3)
_cell_length_b                   16.9621(3)
_cell_length_c                   9.6648(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2780.69(11)
_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 0.997
_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  0.036
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14601
_diffrn_reflns_theta_full        76.493
_diffrn_reflns_theta_max         76.493
_diffrn_reflns_theta_min         3.685
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  0.9472
_exptl_absorpt_correction_T_min  0.9326
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9592
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         11987
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.0011177
_refine_ls_shift/su_mean         0.0000683
_refine_ls_structure_factor_coef Fsqd
_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: 
 0.186E+04 0.314E+04 0.195E+04 831. 188. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1219
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1219
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              -12
_reflns_number_gt                10852
_reflns_number_total             1563
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.85
_oxford_diffrn_Wilson_scale      0.18
_oxford_refine_ls_r_factor_ref   0.0465
_oxford_refine_ls_scale          2.615(16)
_oxford_reflns_number_all        11987
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            jo4020563_si_001_1.cif
_cod_data_source_block           39
_cod_original_cell_volume        2780.71(12)
_cod_original_formula_sum        'C11 H19 N1 O5'
_cod_database_code               4028847
_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 C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE O   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  93,X'S) H   (  92,X'S) H   (  91,X'S) 
RIDE N   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 143,X'S) H   ( 142,X'S) 
RIDE C   (  15,X'S) H   ( 152,X'S) H   ( 151,X'S) H   ( 153,X'S) 
RIDE C   (  16,X'S) H   ( 162,X'S) H   ( 163,X'S) H   ( 161,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                                                                             
;