Diastereoselective Synthesis of the Aminocyclitol Core of Jogyamycin via an Allene Aziridination Strategy.
Gerstner, Nels C.; Adams, Christopher S.; Grigg, R. David; Tretbar, Maik; Rigoli, Jared W.; Schomaker, Jennifer M.; Organic letters 18 (2016) 284–287; doi:10.1021/acs.orglett.5b03453

data_1541914
_publ_section_title
;
 Diastereoselective Synthesis of the Aminocyclitol Core of Jogyamycin via
 an Allene Aziridination Strategy.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              284
_journal_page_last               287
_journal_paper_doi               10.1021/acs.orglett.5b03453
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_compound_source        'Schomaker Lab No. CSA8084'
_chemical_formula_moiety         'C11 H21 N O5 S'
_chemical_formula_sum            'C11 H21 N O5 S'
_chemical_formula_weight         279.35
_chemical_name_systematic
;       
'4-ethyl-5-hydroxy-4-(-2-hydroxy-3-methylbut-3
-en-2-yl)-1,2,3-oxathiazepane 2,2-dioxide'
;
_chemical_properties_physical    air-stable
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
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Olex2 1.2
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_cell_measurement_temperature    100(2)
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_cell_measurement_theta_min      4.7660
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_computing_cell_refinement       'SAINT+ Ver. 8.30C (Bruker-AXS, 2013)'
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_diffrn_radiation_monochromator  'equatorially mounted graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_number            2461
_diffrn_reflns_point_group_measured_fraction_full 0.998
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_diffrn_reflns_theta_full        67.000
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_diffrn_source                   'sealed X-ray tube'
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_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
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_exptl_crystal_description       needle
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_exptl_crystal_recrystallization_method 'dichlormethan, n-hexane'
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_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   0.753299
_exptl_transmission_factor_min   0.648046
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 985 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.154(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0277
_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^)+(0.0442P)^2^+0.5028P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0733
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2412
_reflns_number_total             2461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03453_si_004.cif
_cod_data_source_block           schomaker48
_cod_depositor_comments
'Adding full bibliography for 1541913--1541914.cif.'
_cod_original_cell_volume        1300.6(5)
_cod_database_code               1541914
_shelxl_version_number           2014/6
_shelx_res_checksum              30490
_shelx_hkl_checksum              2178