Scalable Synthesis of Anomerically Pure Orthogonal-Protected GlcN3 and GalN3 from d-Glucosamine.
Glibstrup, Emil; Pedersen, Christian Marcus; Organic letters 18 (2016) 4424–4427; doi:10.1021/acs.orglett.6b02241

data_1555727
_publ_section_title
;
 Scalable Synthesis of Anomerically Pure Orthogonal-Protected GlcN3 and
 GalN3 from d-Glucosamine.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4424
_journal_page_last               4427
_journal_paper_doi               10.1021/acs.orglett.6b02241
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H21 N3 O7 S'
_chemical_formula_sum            'C18 H21 N3 O7 S'
_chemical_formula_weight         423.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-04-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.836(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5129(6)
_cell_length_b                   8.0260(5)
_cell_length_c                   12.3315(7)
_cell_measurement_reflns_used    9130
_cell_measurement_temperature    122(2)
_cell_measurement_theta_max      31.532
_cell_measurement_theta_min      2.793
_cell_volume                     1025.19(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      122(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13396
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.127
_diffrn_reflns_theta_min         2.356
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1501 before and 0.0892 after correction.
The Ratio of minimum to maximum transmission is 0.7963.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       Prism
_exptl_crystal_F_000             444
_exptl_crystal_size_max          1.262
_exptl_crystal_size_mid          0.62
_exptl_crystal_size_min          0.287
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 1775 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4953
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+0.1476P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1111
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_full    0.880
_reflns_Friedel_fraction_max     0.791
_reflns_number_gt                4631
_reflns_number_total             4953
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02241_si_001.cif
_cod_data_source_block           mo_d8v1493_0m-1
_cod_database_code               1555727
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.784
_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:
 C5(H5), C4(H4), C1(H1), C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C15(H15), C14(H14), C18(H18)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              42255
_shelx_hkl_checksum              46219
_olex2_submission_special_instructions 'No special instructions were received'