Conversion of glycals into vicinal-1,2-diazides and 1,2-(or 2,1)-azidoacetates using hypervalent iodine reagents and Me3SiN3. Application in the synthesis of N-glycopeptides, pseudo-trisaccharides and an iminosugar
Chennaiah, Ande; Bhowmick, Srijita; Vankar, Yashwant D.; RSC Adv. 7 (2017) 41755–; doi:10.1039/C7RA08637G

data_7229019
_publ_section_title
;
 Conversion of glycals into vicinal-1,2-diazides and 1,2-(or
 2,1)-azidoacetates using hypervalent iodine reagents and Me3SiN3.
 Application in the synthesis of N-glycopeptides, pseudo-trisaccharides
 and an iminosugar
;
_journal_issue                   66
_journal_name_full               'RSC Adv.'
_journal_page_first              41755
_journal_paper_doi               10.1039/C7RA08637G
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration unknown
_chemical_formula_moiety         'C27 H28 N6 O4'
_chemical_formula_sum            'C27 H28 N6 O4'
_chemical_formula_weight         500.55
_chemical_name_common            'Galctose diazide'
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-06-01 deposited with the CCDC.
2017-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.166(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8746(7)
_cell_length_b                   9.3560(6)
_cell_length_c                   12.7699(9)
_cell_measurement_reflns_used    4239
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.75
_cell_volume                     1234.49(14)
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0882
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12546
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.342
_diffrn_reflns_theta_min         1.971
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1277 before and 0.0538 after correction.
The Ratio of minimum to maximum transmission is 0.8084.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             528.0
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .16
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1450 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         6100
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0572
_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^)+(0.0646P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1351
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                4257
_reflns_number_total             6100
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra08637g2.cif
_cod_data_source_block           28augb_0m
_cod_database_code               7229019
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C23(H23), C21(H21), C22(H22), C20(H20), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C011(H01A,H01B), C012(H01C,H01D), C016(H01E,H01F), C024(H02A,H02B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C10(H10), C9(H9), C8(H8), C17(H17), C16(H16), C15(H15),
 C13(H13), C18(H18), C4(H4), C5(H5), C1(H1), C2(H2), C3(H3)
2.d Fitted hexagon refined as free rotating group:
 C7(C12,C11,C10,C9,C8), C17(C16,C15,C14,C13,C18), C4(C5,C6,C1,C2,C3)
;
_shelx_res_checksum              59724
_olex2_submission_special_instructions 'No special instructions were received'