Research

Synthesis and conformational and configurational studies of diastereoisomeric O-protected 4-(arylsulfonimidoyl)butane-1,2,3-triols


Reference:

Kwong, J. S. W., Mahon, M. F., Lloyd, M. D. and Threadgill, M. D., 2007. Synthesis and conformational and configurational studies of diastereoisomeric O-protected 4-(arylsulfonimidoyl)butane-1,2,3-triols. Tetrahedron, 63 (51), pp. 12601-12607.

Related documents:

[img]
Preview
PDF (author's accepted version) - Requires a PDF viewer such as GSview, Xpdf or Adobe Acrobat Reader
Download (10MB) | Preview

    Official URL:

    http://dx.doi.org/10.1016/j.tet.2007.10.017

    Abstract

    Chiral sulfoximines have applications as transition-state mimicking enzyme inhibitors, as peptide isosteres and as chiral auxiliaries in synthesis. To access the required O-protected 4- (arylsulfonimidoyl)butane-1,2,3-triols, 4S,5S-di(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane (prepared from diethyl R,R-tartrate) was converted into its monobenzyl ether. Mitsunobu-like coupling with thiophenols gave 4S,5R-4-(benzyloxymethyl)-2,2-dimethyl-5-(arylthiomethyl)- 1,3-dioxolanes. Sulfoxidation and S-imination (trifluoroacetamide, iodosobenzene diacetate, rhodium acetate) proceeded without stereoselectivity, giving inseparable diastereomeric mixtures of 4S,5R,S(±)-4-(benzyloxymethyl)-2,2-dimethyl-5-(N-(trifluoroacetyl)arylsulfonimidoylmethyl)- 1,3-dioxolanes. Removal of the trifluoroacetyl protection allowed chromatographic separation of the diastereomeric 4S,5R,S(±)-4-(benzyloxymethyl)-2,2-dimethyl-5- (arylsulfonimidoylmethyl)-1,3-dioxolanes. The configurations at sulfur were determined by X-ray crystallography and some analysis of the solution and solid-state conformations was carried out. The resulting O-protected 4-(arylsulfonimidoyl)butane-1,2,3-triols are of use in developing enzyme inhibitors.

    Details

    Item Type Articles
    CreatorsKwong, J. S. W., Mahon, M. F., Lloyd, M. D. and Threadgill, M. D.
    DOI10.1016/j.tet.2007.10.017
    Uncontrolled Keywordsx-ray crystallography, sulfoximine, butanetriol, diastereoisomer, conformation
    DepartmentsFaculty of Science > Pharmacy & Pharmacology
    Faculty of Science > Chemistry
    Publisher StatementTet%202007%2012601%20revised%20draft%20MDT.pdf: NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron, 63: 51, 2007. doi: 10.1016/j.tet.2007.10.017
    RefereedYes
    StatusPublished
    ID Code403

    Export

    Actions (login required)

    View Item

    Document Downloads

    More statistics for this item...