Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc) and ureido-DNJNAc derivatives as new hexosaminidase inhibitors.
de la Fuente, Alex; Mena-Barragán, Teresa; Farrar-Tobar, Ronald A; Verdaguer, Xavier; García Fernández, José M; Ortiz Mellet, Carmen; Riera, Antoni; Organic & biomolecular chemistry 13 (2015) 6500–6510; doi:10.1039/c5ob00507h

data_7154425
_publ_section_title
;
 Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc)
 and ureido-DNJNAc derivatives as new hexosaminidase inhibitors.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6500
_journal_page_last               6510
_journal_paper_doi               10.1039/c5ob00507h
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H16 N4 O4'
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_audit_update_record
;
2015-03-12 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
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_cell_length_b                   9.745(2)
_cell_length_c                   18.180(4)
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_cell_measurement_theta_min      2.37
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_computing_data_collection       'Bruker APEX2 v2009.1-0'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
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_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support
'magnetic support whith 10 micron nylon fiber cryoloop'
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_diffrn_reflns_av_R_equivalents  0.0481
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_diffrn_reflns_limit_h_max       13
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_diffrn_source                   'rotating anode X-ray tube'
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_diffrn_source_size              '3 mm x 0.3 mm fine focus'
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_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.309
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         7016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1420
_reflns_number_gt                6050
_reflns_number_total             7016
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00507h2.cif
_cod_data_source_block           mo_af115_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_diffrn_measurement_specimen_suppport' tag replaced with
'_diffrn_measurement_specimen_support' tag as specified in the
replacement file
'/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/lists/replacement-tags.lst'.

Automatic conversion script
Id: cif_correct_tags 3376 2015-05-07 07:48:27Z andrius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154425--7154426.cif.
;
_cod_original_cell_volume        1435.2(6)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7154425