A Concise Route to Branched Erythrono-γ-lactones. Synthesis of the Leaf-Closing Substance Potassium (\±)-(2R,3R)-2,3,4-Trihydroxy-2-methylbutanoate
Daniel Sejer Pedersen; Tony V. Robinson; Dennis K. Taylor; Edward R. T. Tiekink; Journal of Organic Chemistry 74 (2009) 4400–4403; doi:10.1021/jo900392y

data_4024558
_publ_section_title
;
A Concise Route to Branched Erythrono-\g-lactones. Synthesis of the
Leaf-Closing Substance Potassium
(\+-)-(2R,3R)-2,3,4-Trihydroxy-2-methylbutanoate
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4400
_journal_page_last               4403
_journal_paper_doi               10.1021/jo900392y
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C17 H26 O4'
_chemical_formula_sum            'C17 H26 O4'
_chemical_formula_weight         294.38
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.370(3)
_cell_length_b                   11.328(2)
_cell_length_c                   21.465(4)
_cell_measurement_reflns_used    4892
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.7
_cell_measurement_theta_min      2.0
_cell_volume                     3007.8(11)
_computing_cell_refinement       CrystalClear
_computing_data_collection
'CrystalClear (Rigaku Americas Corporation, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) & DIAMOND (Brandenburg, 2006)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  AFC12\k/SATURN724
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_sigmaI/netI    0.016
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11519
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.19
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.09
_refine_ls_R_factor_all          0.044
_refine_ls_R_factor_gt           0.042
_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^)+(0.06P)^2^+0.7283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.112
_refine_ls_wR_factor_ref         0.115
_reflns_number_gt                2896
_reflns_number_total             3061
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo900392y_si_002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_Hall     '-P 2ac 2ab  '
_cod_database_code               4024558