A versatile stereocontrolled synthesis of 2-deoxyiminosugar C-glycosides and their evaluation as glycosidase inhibitors.
Lumbroso, Alexandre; Berthonneau, Clément; Beaudet, Isabelle; Quintard, Jean-Paul; Planchat, Aurélien; García-Moreno, M Isabel; Ortiz Mellet, Carmen; Le Grognec, Erwan; Organic & biomolecular chemistry 19 (2021) 1083–1099; doi:10.1039/d0ob02249g

data_7157827
_publ_section_title
;
 A versatile stereocontrolled synthesis of 2-deoxyiminosugar C-glycosides
 and their evaluation as glycosidase inhibitors.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1083
_journal_page_last               1099
_journal_paper_doi               10.1039/d0ob02249g
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C13 H23 N1 O5'
_chemical_formula_sum            'C13 H23 N O5'
_chemical_formula_weight         273.3
_chemical_name_systematic
(1R,5R,6R,7S,8aR)-6,7-dihydroxy-5-(hydroxymethyl)-1-pentylhexahydro-3H-oxazolo[3,4-a]pyridin-3-one
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_update_record
;
2020-10-26 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                91.0(3)
_cell_angle_beta                 93.03(14)
_cell_angle_gamma                90.89(19)
_cell_formula_units_Z            2
_cell_length_a                   4.844(6)
_cell_length_b                   7.64(2)
_cell_length_c                   18.26(2)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    120
_cell_measurement_theta_max      20
_cell_measurement_theta_min      5
_cell_volume                     675(2)
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Nonius CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1007
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14142
_diffrn_reflns_theta_full        27.3
_diffrn_reflns_theta_max         27.3
_diffrn_reflns_theta_min         6.55
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.9777
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'Jana2006  (Petricek, Dusek & Palatinus, 2000)'
_exptl_crystal_density_diffrn    1.3451
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.47
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_gt    1.68
_refine_ls_goodness_of_fit_ref   1.62
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    80
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.0040
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/(\s^2^(I)+0.0025000002I^2^)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                2252
_reflns_number_total             2981
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d0ob02249g2.cif
_cod_data_source_block           I
_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 7157827--7157828.cif.
;
_cod_original_formula_sum        'C13 H23 N1 O5'
_cod_database_code               7157827