Regioselective Reductive Cleavage of Bis-benzylidene Acetal: Stereoselective Synthesis of Anticancer Agent OGT2378 and Glycosidase Inhibitor 1,4-Dideoxy-1,4-imino-l-xylitol
Appu Aravind; Muthukumar Gomathi Sankar; Babu Varghese; Sundarababu Baskaran; Journal of Organic Chemistry 74 (2009) 2858–2861; doi:10.1021/jo900030p

data_4024443
_publ_section_title
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Regioselective Reductive Cleavage of Bis-benzylidene Acetal:
Stereoselective Synthesis of Anticancer Agent OGT2378 and Glycosidase
Inhibitor 1,4-Dideoxy-1,4-imino-l-xylitol
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2858
_journal_page_last               2861
_journal_paper_doi               10.1021/jo900030p
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_formula_sum            'C12 H17 N O5 S'
_chemical_formula_weight         287.33
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.321(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.651(3)
_cell_length_b                   5.5009(11)
_cell_length_c                   19.408(4)
_cell_measurement_reflns_used    2357
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.454
_cell_measurement_theta_min      3.235
_cell_volume                     1349.6(5)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP 32 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare etal., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker Apex2 kappa diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0872
_diffrn_reflns_av_sigmaI/netI    0.0684
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4913
_diffrn_reflns_theta_full        21.37
_diffrn_reflns_theta_max         21.37
_diffrn_reflns_theta_min         1.05
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.9122
_exptl_absorpt_correction_T_min  0.8120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1466
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.182
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0897P)^2^+2.9557P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1517
_refine_ls_wR_factor_ref         0.1704
_reflns_number_gt                1299
_reflns_number_total             1466
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900030p_si_004.cif
_cod_data_source_block           c2
_cod_depositor_comments
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The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_original_sg_symbol_H-M      C2
_cod_database_code               4024443