ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES
RETURN TO ISSUEPREVFeatured ArticleNEXT

A General, Iterative, and Modular Approach toward Carbohydrate Libraries Based on Ruthenium-Catalyzed Oxidative Cyclizations

View Author Information
Institüt für Organische Chemie, Fakultät Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany
Cite this: J. Org. Chem. 2008, 73, 18, 7028–7036
Publication Date (Web):August 16, 2008
https://doi.org/10.1021/jo801528n
Copyright © 2008 American Chemical Society

    Article Views

    3610

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (1)»

    Abstract

    Abstract Image

    Carbohydrates are an omnipresent class of highly oxygenated natural products. Due to their wide spectra of biological activities, they have been in the center of synthetic organic chemistry for more than 130 years. During the past 50 years non-natural carbohydrates attracted the interest of various chemists in the fields of organic, biological, and medical chemistry. Especially desoxygenated sugars proved to be an important class of compounds. Up to date, most non-natural analogues are synthesized starting from natural, enantiomerically pure carbohydrates in multistep synthesis. In this report, we present a synthetic strategy that allows the selective modular synthesis of natural and non-natural carbohydrates within five synthetic steps starting from readily available starting materials. Due to a sequential introduction of O- or N-functionalities, a regioselective protection of each new functional group is possible. The key step in the carbohydrate synthesis is a RuO4-catalyzed oxidative cyclization via a pH-dependent dehydrogenation−dihydroxylation−cyclization or an oxidative fragmentation−cyclization, leading to highly substituted new carbohydrates, in which each functional group is orthogonally protected and accessible for further synthetic operations.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    Experimental procedures for the preparation and spectral data for all reported compounds plus copies of 1H NMR spectra. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 13 publications.

    1. Markus Draskovits, Christian Stanetty, Ian R. Baxendale, and Marko D. Mihovilovic . Indium- and Zinc-Mediated Acyloxyallylation of Protected and Unprotected Aldotetroses—Revealing a Pronounced Diastereodivergence and a Fundamental Difference in the Performance of the Mediating Metal. The Journal of Organic Chemistry 2018, 83 (5) , 2647-2659. https://doi.org/10.1021/acs.joc.7b03063
    2. Suneel P. Singh, Alex Michaelides, A. Rod Merrill, and Adrian L. Schwan . A Microwave-Assisted Synthesis of (S)-N-Protected Homoserine γ-Lactones from l-Aspartic Acid. The Journal of Organic Chemistry 2011, 76 (16) , 6825-6831. https://doi.org/10.1021/jo2008093
    3. Hao Liu, Feiyan Tao, Baoguo Sun, Shaoxiang Yang, Yongguo Liu, Hongyu Tian. Preparation of 3-Methylthiodecanal, a Flavour Compound. Journal of Chemical Research 2015, 39 (12) , 731-733. https://doi.org/10.3184/174751915X14476885268579
    4. Bernd Schmidt, Stefan Krehl. Domino and Other Olefin Metathesis Reaction Sequences. 2014, 187-232. https://doi.org/10.1002/9781118711613.ch5
    5. Vincenzo Piccialli. Ruthenium Tetroxide and Perruthenate Chemistry. Recent Advances and Related Transformations Mediated by Other Transition Metal Oxo-species. Molecules 2014, 19 (5) , 6534-6582. https://doi.org/10.3390/molecules19056534
    6. Bernd Schmidt, Sylvia Hauke. Cross metathesis of allyl alcohols: how to suppress and how to promote double bond isomerization. Organic & Biomolecular Chemistry 2013, 11 (25) , 4194. https://doi.org/10.1039/c3ob40167g
    7. N. Matthias Neisius, Bernd Plietker. Die Ruthenium‐katalysierte Hydrovinylierung interner Alkine mit Acrylsäurederivaten – ein atomökonomischer Zugang zu hochsubstituierten 1,3‐Dienen. Angewandte Chemie 2009, 121 (31) , 5863-5866. https://doi.org/10.1002/ange.200901928
    8. N. Matthias Neisius, Bernd Plietker. The Ruthenium‐Catalyzed Hydrovinylation of Internal Alkynes by Acrylates: An Atom Economic Approach to Highly Substituted 1,3‐Dienes. Angewandte Chemie International Edition 2009, 48 (31) , 5752-5755. https://doi.org/10.1002/anie.200901928
    9. Devendar Rao, Daniel Best, Akihide Yoshihara, Pushpakiran Gullapalli, Kenji Morimoto, Mark R. Wormald, Francis X. Wilson, Ken Izumori, George W.J. Fleet. A concise approach to the synthesis of all twelve 5-deoxyhexoses: d-tagatose-3-epimerase—a reagent that is both specific and general. Tetrahedron Letters 2009, 50 (26) , 3559-3563. https://doi.org/10.1016/j.tetlet.2009.03.061
    10. Faiz Ahmed Khan, Ch. Sudheer. Ruthenium‐Mediated Oxidation under Buffered Conditions: A Simple and Useful Protocol for the Synthesis of Norbornyl α‐Diketones with Acid Sensitive Functionalities. Advanced Synthesis & Catalysis 2009, 351 (6) , 939-944. https://doi.org/10.1002/adsc.200900042
    11. William P. Griffith. The Chemistry of Ruthenium Oxidation Complexes. 2009, 1-134. https://doi.org/10.1007/978-1-4020-9378-4_1
    12. William P. Griffith. Oxidation of Alkenes, Arenes and Alkynes. 2009, 173-213. https://doi.org/10.1007/978-1-4020-9378-4_3
    13. Meike Niggemann, Andreas Jelonek, Nicole Biber, Margarita Wuchrer, Bernd Plietker. ChemInform Abstract: A General, Iterative, and Modular Approach Toward Carbohydrate Libraries Based on Ruthenium‐Catalyzed Oxidative Cyclizations.. ChemInform 2008, 39 (51) https://doi.org/10.1002/chin.200851192

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect