Syntheses of the Enantiomers of 1-Deoxynojirimycin and 1-Deoxyaltronojirimycin via Chemo- and Diastereoselective Olefinic Oxidation of Unsaturated Amines
Sharan K. Bagal; Stephen G. Davies; James A. Lee; Paul M. Roberts; Philip M. Scott; James E. Thomson; Journal of Organic Chemistry 75 (2010) 8133–8146; doi:10.1021/jo101756g

data_4025849
_publ_contact_author_address
;Department of Chemistry
Chemistry Research Laboratory
University of Oxford
Mansfield Road
Oxford
OX1 3TA
U.K.
;
_publ_contact_author_email       sreve.davies@chem.ox.ac.uk
_publ_contact_author_fax         '+44 1865 275633'
_publ_contact_author_name        'Stephen G. Davies'
_publ_contact_author_phone       '+44 1865 275695'
_publ_section_title
;
 Syntheses of the Enantiomers of 1-Deoxynojirimycin and
 1-Deoxyaltronojirimycin via Chemo- and Diastereoselective Olefinic
 Oxidation of Unsaturated Amines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8133
_journal_page_last               8146
_journal_paper_doi               10.1021/jo101756g
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H26.50 Cl1 N1 O2'
_chemical_formula_sum            'C25 H26.5 Cl N O2'
_chemical_formula_weight         408.44
_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
_audit_creation_date             10-05-04
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                64.3905(14)
_cell_angle_beta                 87.8962(14)
_cell_angle_gamma                85.5140(15)
_cell_formula_units_Z            2
_cell_length_a                   9.7315(3)
_cell_length_b                   10.5112(3)
_cell_length_c                   11.3814(4)
_cell_measurement_reflns_used    4574
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1046.61(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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 0.992
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.000
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8261
_diffrn_reflns_theta_full        26.897
_diffrn_reflns_theta_max         27.446
_diffrn_reflns_theta_min         5.363
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             433
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         2.06
_refine_diff_density_min         -1.78
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         6624
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0992
_refine_ls_shift/su_max          0.000078
_refine_ls_structure_factor_coef F
_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: 
 2.08 0.673 1.50 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0940
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0838
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                7182
_reflns_number_total             8261
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.99
_oxford_diffrn_Wilson_scale      1.49
_oxford_refine_ls_r_factor_ref   0.0950
_oxford_refine_ls_scale          0.999(3)
_oxford_reflns_number_all        8259
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_oxford_structure_analysis_title '5041429 SGD293'
_cod_data_source_file            jo101756g_si_003.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 1 '
_cod_original_formula_sum        'C25 H26.50 Cl1 N1 O2'
_cod_database_code               4025849