Furanyl Cyclic Ethers: Single and Double Diastereoselectivity in the Synthesis of 2,4-Di and 2,4,5-Trisubstituted Tetrahydropyrans.
Cooper, Dennis A.; Robbins, Emma; Tizzard, Graham J.; Coles, Simon J.; O'Brien, Matthew; The Journal of organic chemistry 82 (2017) 3441–3455; doi:10.1021/acs.joc.6b02831

data_4032397
_publ_section_title
;
 Furanyl Cyclic Ethers: Single and Double Diastereoselectivity in the
 Synthesis of 2,4-Di and 2,4,5-Trisubstituted Tetrahydropyrans.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3441
_journal_page_last               3455
_journal_paper_doi               10.1021/acs.joc.6b02831
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C18 H22 O5'
_chemical_formula_sum            'C18 H22 O5'
_chemical_formula_weight         318.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
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_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
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;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
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_cell_length_c                   11.9674(18)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
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_diffrn_measurement_details
;
scan:
    Number of images: 129
               Slice: -106.0000 - 23.0000
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            Exp time: 5.0000
       Rotation axis: Omega
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                 XTD: 44.9035
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scan:
    Number of images: 120
               Slice: -97.0000 - 23.0000
         Image width: 1.0000
            Exp time: 5.0000
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scan:
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               Slice: -35.0000 - 69.0000
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            Exp time: 5.0000
       Rotation axis: Omega
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               Kappa: -8.0000
                 Phi: -180.0000
                 XTD: 44.9035
              2theta: -15.6440
scan:
    Number of images: 23
               Slice: -30.0000 - -7.0000
         Image width: 1.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 72.0000
                 Phi: -17.0000
                 XTD: 44.9035
              2theta: -15.6440
scan:
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               Slice: 1.0000 - 16.0000
         Image width: 1.0000
            Exp time: 5.0000
       Rotation axis: Omega
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               Kappa: -40.0000
                 Phi: 49.0000
                 XTD: 44.9035
              2theta: -15.6440
scan:
    Number of images: 129
               Slice: -106.0000 - 23.0000
         Image width: 1.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: -115.0000
                 XTD: 44.9035
              2theta: -15.6440
scan:
    Number of images: 35
               Slice: -97.0000 - -62.0000
         Image width: 1.0000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: 81.0000
                 XTD: 44.9035
              2theta: -15.6440
;
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_diffrn_orient_matrix_UB_22      0.015518
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_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
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_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.986
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_diffrn_reflns_limit_h_max       9
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_diffrn_reflns_limit_k_min       -12
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_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10756
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_diffrn_source                   'Rotating Anode'
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_exptl_crystal_colour            Colorless
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_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0586P)^2^+0.1118P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                3142
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02831_si_002.cif
_cod_data_source_block           3g
_cod_depositor_comments
'Adding full bibliography for 4032395--4032398.cif.'
_cod_database_code               4032397
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C11(H11), C14(H14)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              83235
_shelx_hkl_checksum              34355
_olex2_submission_special_instructions 'No special instructions were received'