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_4021837
_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           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            8
_cell_length_a                   15.041(17)
_cell_length_b                   15.047(17)
_cell_length_c                   14.156(16)
_cell_measurement_temperature    293(2)
_cell_volume                     3204(6)
_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 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20365
_diffrn_reflns_theta_full        25.87
_diffrn_reflns_theta_max         25.87
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelopiped
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(11)
_refine_ls_extinction_coef       0.0217(17)
_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   1.165
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         6081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0568
_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^)+(0.0708P)^2^+0.6267P] where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1422
_reflns_number_gt                5359
_reflns_number_total             6081
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0606554si20060515_023810_2.cif
_cod_database_code               4021837