Zinc-Catalyzed Cycloisomerizations. Synthesis of Substituted Furans and Furopyrimidine Nucleosides
Adam Sniady; Audrey Durham; Marco S. Morreale; Andrzej Marcinek; Slawomir Szafert; Tadeusz Lis; Krystyna R. Brzezinska; Takanori Iwasaki; Takashi Ohshima; Kazushi Mashima; Roman Dembinski; Journal of Organic Chemistry 73 (2008) 5881–5889; doi:10.1021/jo8007995

data_4023585
_publ_contact_author_email       dembinsk@oakland.edu
_publ_contact_author_name        'Roman Dembinski'
_publ_contact_author_phone       +001(248)3702248
_publ_section_title
;
 Zinc-Catalyzed Cycloisomerizations. Synthesis of Substituted Furans
 and Furopyrimidine Nucleosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5881
_journal_page_last               5889
_journal_paper_doi               10.1021/jo8007995
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C14 H18 N2 O5'
_chemical_formula_weight         294.30
_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                   5.684(2)
_cell_length_b                   6.682(2)
_cell_length_c                   36.02(2)
_cell_measurement_reflns_used    12755
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36
_cell_measurement_theta_min      3
_cell_volume                     1368.1(10)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2003)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2003)'
_computing_data_reduction        'CrysAlis RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'Kuma KM-4-CCD \k-geometry'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'medium-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_number            21712
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         36.84
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.58
_refine_diff_density_min         -0.28
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.055P)^2^+0.51P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                3336
_reflns_number_total             3716
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8007995-File004.cif
_cod_data_source_block           for_complex_6b
_cod_database_code               4023585