Stereoselective synthesis of C-glycosides from carboxylic acids: the tandem Tebbe?Claisen approachThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.
Godage, H. Yasmin; Chambers, David J.; Evans, Graham R.; Fairbanks, Antony J.; Organic & Biomolecular Chemistry 1 (2003) 3772–; doi:10.1039/b306675b

data_7151503
_publ_section_title
;
 Stereoselective synthesis of C-glycosides from carboxylic acids: the
 tandem Tebbe?Claisen approachThis is one of a number of contributions
 from the current members of the Dyson Perrins Laboratory to mark the
 end of almost 90 years of organic chemistry research in that building,
 as all its current academic staff move across South Parks Road to a
 new purpose-built laboratory.
;
_journal_issue                   21
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              3772
_journal_paper_doi               10.1039/b306675b
_journal_volume                  1
_journal_year                    2003
_chemical_absolute_configuration syn
_chemical_compound_source
;
synthesis as described
;
_chemical_formula_moiety         ' C22 H32 O4 Si1 '
_chemical_formula_sum            'C22 H32 O4 Si'
_chemical_formula_weight         388.58
_chemical_melting_point          ?
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 94.0089(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4698(2)
_cell_length_b                   6.4952(2)
_cell_length_c                   20.0695(4)
_cell_measurement_reflns_used    10755
_cell_measurement_temperature    150
_cell_measurement_theta_max      28
_cell_measurement_theta_min      5
_cell_volume                     1101.38(5)
_computing_cell_refinement
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_data_collection
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_publication_material
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_refinement
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Nonius KappaCCD
;
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10755
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         5.10
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_meas      ?
_exptl_crystal_description       ' plate '
_exptl_crystal_F_000             420.248
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0489
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2140
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.006034
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979)
2.63    -1.35     1.79
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0373
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                2140
_reflns_number_total             2712
_reflns_threshold_expression     >3.00\s(I)
_cod_data_source_file            b306675b.txt
_cod_data_source_block           CRYSTALS_cif_a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic ' changed to 'monoclinic'
according to '/home/adriana/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 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        ' C22 H32 O4 Si1 '
_cod_database_code               7151503