A neighboring group participation strategy: direct and highly diastereoselective synthesis of 2-substituted and 2,2-bisubstituted perhydrofuro[2,3-b]pyran derivatives.
Ma, Xiaofeng; Tang, Qin; Ke, Jun; Zhang, Jichao; Yang, Xinglong; Shen, Xudong; Shao, Huawu; Organic & biomolecular chemistry 12 (2014) 7381–7388; doi:10.1039/c4ob00642a

data_7154049
_publ_section_title
;
 A neighboring group participation strategy: direct and highly
 diastereoselective synthesis of 2-substituted and 2,2-bisubstituted
 perhydrofuro[2,3-b]pyran derivatives.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7381
_journal_page_last               7388
_journal_paper_doi               10.1039/c4ob00642a
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C12 H22 O5'
_chemical_formula_sum            'C12 H22 O5'
_chemical_formula_weight         246.30
_chemical_name_systematic
;
?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-11-01
_audit_creation_method
;
Olex2 1.1
(compiled 2011.09.07 svn.r1971, GUI svn.r3853)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.122(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.2466(4)
_cell_length_b                   6.8285(6)
_cell_length_c                   16.0444(15)
_cell_measurement_reflns_used    771
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1985
_cell_measurement_theta_min      3.2371
_cell_volume                     682.60(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
1 omega 13.00 50.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- -17.0486 77.0000 -120.0000 37

2 omega -47.00 -15.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- -17.0486 77.0000 -120.0000 32

3 omega -9.00 56.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 20.0174 77.0000 60.0000 65

4 omega -4.00 82.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 20.0174 77.0000 -60.0000 86

5 omega -52.00 -27.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 20.0174 -38.0000 -30.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0643024000
_diffrn_orient_matrix_UB_12      0.0443384000
_diffrn_orient_matrix_UB_13      -0.0330255000
_diffrn_orient_matrix_UB_21      0.0918427000
_diffrn_orient_matrix_UB_22      0.0111806000
_diffrn_orient_matrix_UB_23      -0.0230931000
_diffrn_orient_matrix_UB_31      -0.0195638000
_diffrn_orient_matrix_UB_32      -0.0933096000
_diffrn_orient_matrix_UB_33      -0.0184504000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2891
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.24
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2004
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0748
_refine_ls_shift/su_max          11.287
_refine_ls_shift/su_mean         0.057
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1299P)^2^+0.0869P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1934
_refine_ls_wR_factor_ref         0.2271
_reflns_number_gt                1356
_reflns_number_total             2004
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7153973
_cod_data_source_file            c4ob00642a2.cif
_cod_data_source_block           111028_s1_mxf
_cod_database_code               7154049
_chemical_oxdiff_formula         C20H20O5
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32