Efficient synthesis of a galectin inhibitor clinical candidate (TD139) using a Payne rearrangement/azidation reaction cascade.
St-Gelais, Jacob; Denavit, Vincent; Giguère, Denis; Organic & biomolecular chemistry 18 (2020) 3903–3907; doi:10.1039/d0ob00910e

data_7157496
_publ_section_title
;
 Efficient synthesis of a galectin inhibitor clinical candidate (TD139)
 using a Payne rearrangement/azidation reaction cascade.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3903
_journal_page_last               3907
_journal_paper_doi               10.1039/d0ob00910e
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C12 H16 O8), 1.25(H2 O)'
_chemical_formula_sum            'C24 H34.5 O17.25'
_chemical_formula_weight         599.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
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;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-30 deposited with the CCDC.	2020-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_length_c                   10.9617(5)
_cell_measurement_reflns_used    9836
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.725
_cell_measurement_theta_min      3.606
_cell_volume                     1251.81(10)
_computing_cell_refinement
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
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_diffrn_reflns_point_group_measured_fraction_full 0.997
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'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0970 before and 0.0601 after correction. The Ratio of minimum to maximum transmission is 0.8760. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
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_exptl_crystal_recrystallization_method 'crystallized in Acetone/Heptane'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.135
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.161(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
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_refine_ls_hydrogen_treatment    mixed
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_refine_ls_R_factor_all          0.0507
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_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^)+(0.0879P)^2^+0.3397P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1176
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2859
_reflns_number_total             2861
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00910e2.cif
_cod_data_source_block           dgige8
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157496.cif.
;
_cod_original_formula_sum        'C24 H34.50 O17.25'
_cod_database_code               7157496
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.834
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.0(2)
 -0.0(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H,H) groups
3. Restrained distances
 O2-H2 = O7-H7 = O9-H9A
 0.85 with sigma of 0.002
 O2-H2 \\sim O7-H7 \\sim O9-H9A
 with sigma of 0.002
4. Others
 Fixed Sof: O10(0.125) H10A(0.125) H10B(0.125)
5.a Riding coordinates:
 O10(H10A,H10B)
5.b Ternary CH refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C6(H6), C7(H7A), C8(H8), C9(H9), C10(H10),
 C12(H12)
5.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C11(H11A,H11B)
;
_shelx_res_checksum              87840
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
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_olex2_submission_special_instructions 'No special instructions were received'