A stereoselective route toward polyhydoxylated piperidines. A total synthesis of (+/-)-deoxymannojirimycin.
Boglio, Cécile; Stahlke, Sebastian; Thorimbert, Serge; Malacria, Max; Organic letters 7 (2005) 4851–4854; doi:10.1021/ol051745i

data_1506710
_publ_section_title
;
 A stereoselective route toward polyhydoxylated piperidines. A total
 synthesis of (+/-)-deoxymannojirimycin.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              4851
_journal_page_last               4854
_journal_paper_doi               10.1021/ol051745i
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C23 H37 N O8 S Si'
_chemical_formula_sum            'C23 H37 N O8 S Si'
_chemical_formula_weight         515.69
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_date             2005-07-21T09:22:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 98.096(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5810(17)
_cell_length_b                   14.2050(10)
_cell_length_c                   14.3610(18)
_cell_measurement_reflns_used    180
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      21.2
_cell_measurement_theta_min      3.8
_cell_volume                     2742.9(5)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            50118
_diffrn_reflns_theta_full        30
_diffrn_reflns_theta_max         30
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.312
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         7978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+0.7617P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1447
_reflns_number_gt                4766
_reflns_number_total             7978
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051745isi20050725_060215.cif
_cod_data_source_block           bs34c
_cod_depositor_comments
;
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1506710