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Carbohydr Res. 2013 Apr 5;370:19-23. doi: 10.1016/j.carres.2013.01.007. Epub 2013 Jan 23.

Improved and large-scale synthesis of different protected D-glucuronals.

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  • 1Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna 1060, Austria. hannes.mikula@tuwien.ac.at

Abstract

Although different protected D-glucuronals are used as precursors for the preparation of many compounds, standard procedures and large-scale syntheses are still not described in the literature. In the course of the development of different protected d-glucuronyl donors we developed several versatile methods that can be used for fast and reproducible preparation of large amounts of the key intermediates. D-Glucuronolactone was converted to methyl 3,4-di-O-acetyl-D-glucuronal applying a novel one-pot protocol, which allowed for large-scale synthesis. Introduction of silyl and benzyl groups was achieved using optimized procedures. Furthermore 3,4,6-tri-O-acetyl-D-glucal was used as starting material for an improved preparation of benzyl protected D-glucuronal, which significantly accelerates and simplifies similar methods described in the literature.

Copyright © 2013 Elsevier Ltd. All rights reserved.

PMID:
23419943
[PubMed - indexed for MEDLINE]
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