Lewis Acid Induced Anomerization of Se-Glycosides. Application to Synthesis of α-Se-GalCer.
McDonagh, Anthony W.; Mahon, Mary F.; Murphy, Paul V.; Organic letters 18 (2016) 552–555; doi:10.1021/acs.orglett.5b03591

data_1542306
_publ_section_title
;
 Lewis Acid Induced Anomerization of Se-Glycosides. Application to
 Synthesis of \a-Se-GalCer.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              552
_journal_page_last               555
_journal_paper_doi               10.1021/acs.orglett.5b03591
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C31 H30 O9 Se'
_chemical_formula_sum            'C31 H30 O9 Se'
_chemical_formula_weight         625.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-09-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.22509(5)
_cell_length_b                   17.41592(17)
_cell_length_c                   26.9154(2)
_cell_measurement_reflns_used    20126
_cell_measurement_temperature    277.74(10)
_cell_measurement_theta_max      71.8070
_cell_measurement_theta_min      5.0920
_cell_volume                     2918.05(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      277.74(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
?
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0512634000
_diffrn_orient_matrix_UB_12      -0.0483026000
_diffrn_orient_matrix_UB_13      -0.0464656000
_diffrn_orient_matrix_UB_21      0.1221571000
_diffrn_orient_matrix_UB_22      0.0685370000
_diffrn_orient_matrix_UB_23      -0.0226242000
_diffrn_orient_matrix_UB_31      0.2089736000
_diffrn_orient_matrix_UB_32      -0.0281923000
_diffrn_orient_matrix_UB_33      0.0246221000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            36496
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.017
_diffrn_reflns_theta_min         5.079
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.1819
_exptl_crystal_size_mid          0.0727
_exptl_crystal_size_min          0.0304
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2301 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         5733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0329P)^2^+0.6326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0650
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                5532
_reflns_number_total             5733
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03591_si_001.cif
_cod_data_source_block           s15pma1
_cod_depositor_comments          'Adding full bibliography for 1542306.cif.'
_cod_database_code               1542306
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'Cu1 N2 B1 C28 H44'
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C31(H31A,H31B,H31C)
;