Glycoscience pp 737-753 | Cite as

Anomeric Anhydro Sugars

  • Nathan W. McGill
  • Spencer J. WilliamsEmail author


Anomeric anhydro sugars are sugar derivatives where the anomeric carbon participates in an acetal linkage with two of the hydroxyl groups of the sugar. They are essentially intramolecular glycosides, and their bicyclic nature provides a powerful conformational constraint that greatly influences their reactivity. This chapter reviews the occurrence, properties, formation, and reactions of anomeric anhydro sugars. Particular emphasis is placed on 1,2- and 1,6‑anhydropyranoses, including conformational aspects and ring‐opening reactions. Epoxide‐containing 1,6‑anhydro sugars (Černý epoxides) are briefly reviewed, and the formation and some reactions of the 1,6‑anhydro sugar enone, levoglucosenone, is covered. An overview is given of the use of 1,2‑anhydro sugar as glycosyl donors. Also discussed are the formation and reactions of anomeric anhydro sugars containing nitrogen, sulfur, or selenium.


Anhydro sugars Dianhydro sugars Epoxide Glucosan Glycosan Levoglucosan Levoglucosenone Seleno sugar Selenolevoglucosan Thiolevoglucosan 



camphorsulfonic acid








triethylsilyl triflate


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Copyright information

© Springer-Verlag Berlin Heidelberg New York 2008

Authors and Affiliations

  1. 1.School of ChemistryThe University of MelbourneParkvilleAustralia

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