Debenzylative Cycloetherification as a Synthetic Tool in the Diastereoselective Synthesis of 3,6-Disubstituted Hexahydro-2<i>H</i>-furo[3,2-<i>b</i>]pyrroles, PDE1 Enzyme Inhibitors with an Antiproliferative Effect on Melanoma Cells.
Castán, Alejandro; Badorrey, Ramón; Díez, José A; Christoffersen, Claus T.; Rasmussen, Lars K.; Kehler, Jan; Köhler, Ralf; Gálvez, José A; Díaz-de-Villegas, María D; The Journal of organic chemistry 85 (2020) 5941–5951; doi:10.1021/acs.joc.0c00276

data_4038269
_publ_section_title
;
 Debenzylative Cycloetherification as a Synthetic Tool in the
 Diastereoselective Synthesis of 3,6-Disubstituted
 Hexahydro-2<i>H</i>-furo[3,2-<i>b</i>]pyrroles, PDE1 Enzyme Inhibitors
 with an Antiproliferative Effect on Melanoma Cells.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5941
_journal_page_last               5951
_journal_paper_doi               10.1021/acs.joc.0c00276
_journal_volume                  85
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C18 H25 N O5'
_chemical_formula_sum            'C18 H25 N O5'
_chemical_formula_weight         335.39
_chemical_name_systematic
; 
tert-butyl (3S,3aS,6R,6aR)-3-(benzyloxy)-6-hydroxyhexahydro-4H-furo[3,2-b]pyrrole-4-carboxylate 
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_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                   8.6708(15)
_cell_length_b                   11.5329(18)
_cell_length_c                   17.874(3)
_cell_measurement_reflns_used    3112
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.2400
_cell_measurement_theta_min      3.4600
_cell_volume                     1787.4(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14059
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         28.82
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+0.4050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1266
_reflns_number_gt                3135
_reflns_number_total             4196
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00276_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4038269.cif.
;
_cod_database_code               4038269