Stereoselective Synthesis of α‐Glycosyl Azides by TMSOTf‐Mediated Ring Opening of 1, 6‐Anhydro Sugars. Issue 10 (18th February 2013)

• Record Type: Journal Article
• Authors: Lepage, Mathieu L.; Bodlenner, Anne; Compain, Philippe
• Is Part Of: European journal of organic chemistry. Issue 10(2013)
• Page Start: 1963
• Page End: 1972
• Publication Date: 2013-02-18
• Subjects: Synthetic methods -- Carbohydrates -- Glycosides -- Azides -- Click chemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201201580
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Access to α‐glycosyl azides in modest to high diastereoselectivity by way of TMSN3 ring‐opening of 1, 6‐anhydro sugars mediated by TMSOTf is reported. The reaction tolerates a wide variety of functional groups including alcohol, alkyne, azide and ester groups. The efficient synthesis of a pseudopentasaccharide in five steps from commercially available levoglucosan by way of a "click‐click" approach is presented to highlight the interest of the TMSN3 ring‐opening reaction. Abstract : A new route to α‐glycosyl azides by way of TMSN3 ring‐opening of 1, 6‐anhydro sugars is presented. The potential of this methodology is demonstrated by the expeditious synthesis of a pseudopentasaccharide following a "click‐click" approach.