Synthesis of l-Iduronic Acid Derivatives via [3.2.1] and [2.2.2] l-Iduronic Lactones from Bulk Glucose-Derived Cyanohydrin Hydrolysis: A Reversible Conformationally Switched Superdisarmed/Rearmed Lactone Route to Heparin Disaccharides.
Hansen, Steen U.; Dalton, Charlotte E.; Baráth, Marek; Kwan, Glenn; Raftery, James; Jayson, Gordon C.; Miller, Gavin J.; Gardiner, John M.; The Journal of organic chemistry 80 (2015) 3777–3789; doi:10.1021/jo502776f

data_4030928
_publ_section_title
;
 Synthesis of l-Iduronic Acid Derivatives via [3.2.1] and [2.2.2]
 l-Iduronic Lactones from Bulk Glucose-Derived Cyanohydrin Hydrolysis: A
 Reversible Conformationally Switched Superdisarmed/Rearmed Lactone Route
 to Heparin Disaccharides.
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_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3777
_journal_page_last               3789
_journal_paper_doi               10.1021/jo502776f
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H20 O7'
_chemical_formula_weight         312.31
_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                87.880(2)
_cell_angle_beta                 68.770(2)
_cell_angle_gamma                76.367(2)
_cell_formula_units_Z            4
_cell_length_a                   10.5288(3)
_cell_length_b                   11.2256(3)
_cell_length_c                   14.5218(3)
_cell_measurement_reflns_used    5032
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      72.23
_cell_measurement_theta_min      3.27
_cell_volume                     1552.59(7)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.942
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0833
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11802
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         72.23
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  0.9316
_exptl_absorpt_correction_T_min  0.630917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.27(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     798
_refine_ls_number_reflns         7612
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0777
_refine_ls_shift/su_max          0.065
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1596P)^2^+0.2452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2228
_refine_ls_wR_factor_ref         0.2377
_reflns_number_gt                6433
_reflns_number_total             7612
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502776f_si_002.cif
_cod_data_source_block           s3749ma
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/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 3143 2015-03-26 13:38:13Z robertas 

 Adding full bibliography for 4030927--4030929.cif.
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_cod_original_sg_symbol_H-M      P1
_cod_database_code               4030928