Synthesis of 1,2-cis-Homoiminosugars Derived from GlcNAc and GalNAc Exploiting a β-Amino Alcohol Skeletal Rearrangement.
Blériot, Yves; Auberger, Nicolas; Jagadeesh, Yerri; Gauthier, Charles; Prencipe, Giuseppe; Tran, Anh Tuan; Marrot, Jérôme; Désiré, Jérôme; Yamamoto, Arisa; Kato, Atsushi; Sollogoub, Matthieu; Organic letters 16 (2014) 5512–5515; doi:10.1021/ol502926f

data_1518071
_publ_section_title
;
 Synthesis of 1,2-cis-Homoiminosugars Derived from GlcNAc and GalNAc
 Exploiting a \b-Amino Alcohol Skeletal Rearrangement.
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_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5512
_journal_page_last               5515
_journal_paper_doi               10.1021/ol502926f
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C17 H26 N2 O9'
_chemical_formula_weight         402.40
_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                84.776(2)
_cell_angle_beta                 82.397(2)
_cell_angle_gamma                83.744(2)
_cell_formula_units_Z            1
_cell_length_a                   5.0198(3)
_cell_length_b                   9.5967(6)
_cell_length_c                   10.9206(7)
_cell_measurement_reflns_used    4309
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.94
_cell_measurement_theta_min      2.74
_cell_volume                     516.78(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12343
_diffrn_reflns_theta_full        24.90
_diffrn_reflns_theta_max         24.90
_diffrn_reflns_theta_min         1.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_correction_T_min  0.9793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2.10)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             214
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         1776
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0860P)^2^+0.0695P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                1479
_reflns_number_total             1776
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502926f_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 1518071.cif.
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_cod_original_sg_symbol_H-M      P1
_cod_database_code               1518071