Highly Diastereoselective Enolate Addition of O-Protected α-Hydroxyacetate to (S~R~)-tert-Butanesulfinylimines: Synthesis of Taxol Side Chain
Yin Wang; Qin-Fei He; Hao-Wei Wang; Xuan Zhou; Zhi-Yan Huang; Yong Qin; Journal of Organic Chemistry 71 (2006) 1588–1591; doi:10.1021/jo052298n

data_4021509
_publ_section_title
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 Highly Diastereoselective Enolate Addition of O-Protected
 \a-Hydroxyacetate to (S~R~)-tert-Butanesulfinylimines:
 Synthesis of Taxol Side Chain
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1588
_journal_page_last               1591
_journal_paper_doi               10.1021/jo052298n
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C25 H31 N O6 S'
_chemical_formula_weight         473.57
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.566(1)
_cell_length_b                   12.145(2)
_cell_length_c                   23.348(4)
_cell_measurement_reflns_used    34
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      14.70
_cell_measurement_theta_min      3.11
_cell_volume                     2712.53(65)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6633
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        2.61
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_correction_T_min  0.9238
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.58
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(8)
_refine_ls_extinction_coef       0.0179(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5540
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0913
_reflns_number_gt                3755
_reflns_number_total             5540
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052298nsi20051105_114815.cif
_cod_depositor_comments
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The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_database_code               4021509