Synthesis and Scalable Conversion of l-Iduronamides to Heparin-Related Di- and Tetrasaccharides
Steen U. Hansen; Gavin J. Miller; Marek Baráth; Karl R. Broberg; Egle Avizienyte; Madeleine Helliwell; James Raftery; Gordon C. Jayson; John M. Gardiner; Journal of Organic Chemistry 77 (2012) 7823–7843; doi:10.1021/jo300722y

data_4027479
_publ_contact_author_address
; 
Department of Chemistry 
University of Manchester 
Manchester M13 9PL 
England  UK 
;
_publ_contact_author_email       jrtest@spec.ch.man.ac.uk
_publ_contact_author_fax         44(161)275-4734
_publ_contact_author_name        'Raftery, James'
_publ_contact_author_phone       44(161)275-4700
_publ_section_title
;
 Synthesis and Scalable Conversion of l-Iduronamides to Heparin-Related
 Di- and Tetrasaccharides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7823
_journal_page_last               7843
_journal_paper_doi               10.1021/jo300722y
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H22 O9'
_chemical_formula_sum            'C18 H22 O9'
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_symmetry_cell_setting           monoclinic
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_atom_sites_solution_hydrogens   geom
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_atom_sites_solution_secondary   difmap
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_cell_angle_alpha                90.00
_cell_angle_beta                 97.034(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.405(3)
_cell_length_b                   5.4897(14)
_cell_length_c                   27.102(5)
_cell_measurement_reflns_used    653
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.7673
_cell_measurement_theta_min      1.6506
_cell_volume                     1831.7(7)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0741
_diffrn_reflns_av_sigmaI/netI    0.2045
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9260
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55446
_exptl_absorpt_correction_type   multi-scan
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         6132
_refine_ls_number_restraints     469
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.1858
_refine_ls_R_factor_gt           0.0923
_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^)+(0.0743P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1834
_refine_ls_wR_factor_ref         0.2372
_reflns_number_gt                3128
_reflns_number_total             6132
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300722y_si_004.cif
_cod_data_source_block           s3551-sm
_cod_original_cell_volume        1831.8(7)
_cod_original_sg_symbol_Hall     P2yb
_cod_database_code               4027479