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_7229018
_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 RS
_chemical_formula_moiety         'C21 H23 N3 O5, C H Cl3'
_chemical_formula_sum            'C22 H24 Cl3 N3 O5'
_chemical_formula_weight         516.79
_chemical_name_systematic        'azido acetate'
_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     dual
_audit_creation_date             2017-06-02
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8335(4)
_cell_length_b                   14.0885(6)
_cell_length_c                   17.7805(9)
_cell_measurement_reflns_used    8477
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.42
_cell_measurement_theta_min      2.37
_cell_volume                     2463.30(19)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       empirical
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22921
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.986
_diffrn_reflns_theta_min         2.291
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5924
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       needle
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.069
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Flack x determined using 1444 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.201
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0616
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1772
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4150
_reflns_number_total             5371
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra08637g2.cif
_cod_data_source_block           2jand_0m
_cod_database_code               7229018
_shelx_shelxl_version_number     2016/6
_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:
 C3(H3), C4(H4), C5(H5), C1(H1), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C13(H13A,H13B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C18(H18), C17(H17), C16(H16), C15(H15), C12(H12), C8(H8), C9(H9),
 C10(H10), C11(H11)
2.d Fitted hexagon refined as free rotating group:
 C19(C18,C17,C16,C15,C14), C12(C7,C8,C9,C10,C11)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              99991
_olex2_submission_special_instructions 'No special instructions were received'