• Login
    View Item 
    •   Home
    • The Christie Research Publications Repository
    • All Christie Publications
    • View Item
    •   Home
    • The Christie Research Publications Repository
    • All Christie Publications
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    Browse

    All of ChristieCommunitiesTitleAuthorsIssue DateSubmit DateSubjectsThis CollectionTitleAuthorsIssue DateSubmit DateSubjectsProfilesView

    My Account

    LoginRegister

    Local Links

    The Christie WebsiteChristie Library and Knowledge Service

    Statistics

    Display statistics

    Scalable synthesis of L-iduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides.

    • CSV
    • RefMan
    • EndNote
    • BibTex
    • RefWorks
    Authors
    Hansen, Steen Uldall
    Baráth, Marek
    Salameh, Bader A B
    Pritchard, Robin G
    Stimpson, William T
    Gardiner, John M
    Jayson, Gordon C
    Affiliation
    School of Chemistry and Manchester Interdisciplinary Biocentre, The University of Manchester, 131 Princess Street, Manchester M1 7DN, UK. gardiner@manchester.ac.uk
    Issue Date
    2009-10-15
    
    Metadata
    Show full item record
    Abstract
    L-ido cyanohydrin 3 was prepared from diacetone-D-glucose in four steps and 76% overall yield and 90% de via cyanohydrin reaction of aldehyde 2. This process can be scaled to provide >1 mol of pure L-ido cyanohydrin 3. Cyanohydrin 3 was elaborated to 1,2-isopropylidine-protected L-ido nitrile (8), iduronic amide 9, and known carboxy ester 10. Coupling of 8 and 9 with glucosamine donors leads to new types (6-cyano and 6-carboxamide) of heparin-related disaccharides.
    Citation
    Scalable synthesis of L-iduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides. 2009, 11 (20):4528-31 Org. Lett.
    Journal
    Organic Letters
    URI
    http://hdl.handle.net/10541/109286
    DOI
    10.1021/ol901723m
    PubMed ID
    19764712
    Type
    Article
    Language
    en
    ISSN
    1523-7052
    ae974a485f413a2113503eed53cd6c53
    10.1021/ol901723m
    Scopus Count
    Collections
    All Christie Publications
    Medical Oncology

    entitlement

    Related articles

    • Synthesis of L-iduronic acid derivatives via [3.2.1] and [2.2.2] L-iduronic lactones from bulk glucose-derived cyanohydrin hydrolysis: a reversible conformationally switched superdisarmed/rearmed lactone route to heparin disaccharides.
    • Authors: Hansen SU, Dalton CE, Baráth M, Kwan G, Raftery J, Jayson GC, Miller GJ, Gardiner JM
    • Issue date: 2015 Apr 17
    • Synthesis and scalable conversion of L-iduronamides to heparin-related di- and tetrasaccharides.
    • Authors: Hansen SU, Miller GJ, Baráth M, Broberg KR, Avizienyte E, Helliwell M, Raftery J, Jayson GC, Gardiner JM
    • Issue date: 2012 Sep 21
    • Synthesis of the basic disaccharide unit of heparin.
    • Authors: Jaurand G, Tabeur C, Petitou M
    • Issue date: 1994 Mar 4
    • Synthesis of a heparin-related GlcN-IdoA sulfation-site variable disaccharide library and analysis by Raman and ROA spectroscopy.
    • Authors: Miller GJ, Hansen SU, Baráth M, Johannessen C, Blanch EW, Jayson GC, Gardiner JM
    • Issue date: 2014 Dec 5
    • Synthesis of disaccharide fragments of the AT-III binding domain of heparin and their sulfonatomethyl analogues.
    • Authors: Herczeg M, Lázár L, Mándi A, Borbás A, Komáromi I, Lipták A, Antus S
    • Issue date: 2011 Sep 27
    DSpace software (copyright © 2002 - 2025)  DuraSpace
    Quick Guide | Contact Us
    Open Repository is a service operated by 
    Atmire NV
     

    Export search results

    The export option will allow you to export the current search results of the entered query to a file. Different formats are available for download. To export the items, click on the button corresponding with the preferred download format.

    By default, clicking on the export buttons will result in a download of the allowed maximum amount of items.

    To select a subset of the search results, click "Selective Export" button and make a selection of the items you want to export. The amount of items that can be exported at once is similarly restricted as the full export.

    After making a selection, click one of the export format buttons. The amount of items that will be exported is indicated in the bubble next to export format.