Stereoselective and Efficient Total Synthesis of Optically Active Tetrodotoxin from D-Glucose
Ken-ichi Sato; Shoji Akai; Hirotsugu Shoji; Naoki Sugita; Shiho Yoshida; Yoshinao Nagai; Katsuhiko Suzuki; Yutaka Nakamura; Yasuhiro Kajihara; Masuo Funabashi; Juji Yoshimura; Journal of Organic Chemistry 73 (2008) 1234–1242; doi:10.1021/jo701655v

data_4023249
_publ_contact_author_email       akais001@kanagawa-u.ac.jp
_publ_contact_author_fax         81-45-413-9770
_publ_contact_author_name        'Shoji Akai'
_publ_contact_author_phone       '81-45-481-5661 ext 3852'
_publ_section_title
;
 Stereoselective and Efficient Total Synthesis of
 Optically Active Tetrodotoxin from D-Glucose
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1234
_journal_page_last               1242
_journal_paper_doi               10.1021/jo701655v
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C33 H45 N3 O8 Si '
_chemical_formula_sum            'C33 H45 N3 O8 Si'
_chemical_formula_weight         639.82
_chemical_melting_point          382
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_date             2006-06-29
_audit_creation_method           'by CrystalStructure 3.7.0'
_audit_update_record             2007-04-16
_cell_angle_alpha                90.0000
_cell_angle_beta                 110.727(5)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   11.727(13)
_cell_length_b                   12.211(12)
_cell_length_c                   12.988(14)
_cell_measurement_reflns_used    5457
_cell_measurement_temperature    113.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     1739(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13654
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             684.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.85
_refine_diff_density_min         -0.58
_refine_ls_abs_structure_details rm
_refine_ls_abs_structure_Flack   0
_refine_ls_extinction_coef       43(36)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     452
_refine_ls_number_reflns         4041
_refine_ls_R_factor_gt           0.0720
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0014Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1936
_reflns_number_gt                2078
_reflns_number_total             4041
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo701655v-File004.cif
_cod_data_source_block           Compound_22(C)
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C33 H45 N3 O8 Si '
_cod_database_code               4023249