Sequential Ring-Closing Metathesis and Nitrone Cycloaddition on Glucose-Derived Substrates: A Divergent Approach to Analogues of Spiroannulated Carbanucleosides and Conformationally Locked Nucleosides
Sk. Sahabuddin; Ashim Roy; Michael G. B. Drew; Biswajit Gopal Roy; Basudeb Achari; Sukhendu B. Mandal; Journal of Organic Chemistry 71 (2006) 5980–5992; doi:10.1021/jo0606554

data_4021836
_publ_section_title
;
 Sequential Ring-Closing Metathesis and Nitrone Cycloaddition on
 Glucose-Derived Substrates: A Divergent Approach to Analogues of
 Spiroannulated Carbanucleosides and Conformationally Locked Nucleosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5980
_journal_page_last               5992
_journal_paper_doi               10.1021/jo0606554
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C17 H23 N O4'
_chemical_formula_weight         305.36
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.190(10)
_cell_angle_beta                 91.880(10)
_cell_angle_gamma                108.790(10)
_cell_formula_units_Z            1
_cell_length_a                   5.502(7)
_cell_length_b                   6.094(7)
_cell_length_c                   12.278(14)
_cell_measurement_temperature    293(2)
_cell_volume                     387.3(8)
_computing_cell_refinement       XDS
_computing_data_collection       'XDS (Kabsch, 1988)'
_computing_data_reduction        XDS
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.896
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_device       'Marresearch Image Plate'
_diffrn_measurement_method
'95 frames at 2 degree intervals, counting time 2 min.'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2424
_diffrn_reflns_theta_full        25.75
_diffrn_reflns_theta_max         25.75
_diffrn_reflns_theta_min         3.55
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelopiped
_exptl_crystal_F_000             164
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.239
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2424
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.238
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;

  w=1/[\s^2^(Fo^2^)+(0.0492P)^2^+0.0396P] where P=(Fo^2^+2Fc^2^)/3 

;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                2374
_reflns_number_total             2424
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0606554si20060515_023810_1.cif
_cod_original_formula_sum        'C17 H23 N O4         '
_cod_database_code               4021836