d-Idose, d-Iduronic Acid, and d-Idonic Acid from d-Glucose via Seven-Carbon Sugars

Zilei Liu; Sarah F. Jenkinson; Akihide Yoshihara; Mark R. Wormald; Ken Izumori; George W. J. Fleet

doi:10.3390/molecules24203758

Molecules (Oct 2019)

d-Idose, d-Iduronic Acid, and d-Idonic Acid from d-Glucose via Seven-Carbon Sugars

Zilei Liu,
Sarah F. Jenkinson,
Akihide Yoshihara,
Mark R. Wormald,
Ken Izumori,
George W. J. Fleet

Affiliations

Zilei Liu: Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford OX1 3TA, UK
Sarah F. Jenkinson: Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford OX1 3TA, UK
Akihide Yoshihara: International Institute of Rare Sugar Research and Education, Kagawa University, Kagawa 761-0795, Japan
Mark R. Wormald: Oxford Glycobiology Institute, Department of Biochemistry, University of Oxford, Oxford OX1 3QU, UK
Ken Izumori: International Institute of Rare Sugar Research and Education, Kagawa University, Kagawa 761-0795, Japan
George W. J. Fleet: Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford OX1 3TA, UK

DOI: https://doi.org/10.3390/molecules24203758
Journal volume & issue: Vol. 24, no. 20
p. 3758

Abstract

Read online

A practical synthesis of the very rare sugar d-idose and the stable building blocks for d-idose, d-iduronic, and d-idonic acids from ido-heptonic acid requires only isopropylidene protection, Shing silica gel-supported periodate cleavage of the C6-C7 bond of the heptonic acid, and selective reduction of C1 and/or C6. d-Idose is the most unstable of all the aldohexoses and a stable precursor which be stored and then converted under very mild conditions into d-idose is easily prepared.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

About the journal

Abstract

Keywords