Iodine: A versatile reagent in carbohydrate chemistry IV. Per-O-Acetylation, regioselective acylation and acetolysis

K.P.R. Kartha, R.A. Field

Research output: Contribution to journalArticlepeer-review

Abstract

Iodine has been found to be an effective Lewis acid for promoting the per-O-acetylation of unprotected sugars. Under controlled conditions it can bring about regioselective acylation of carbohydrate derivatives. At higher concentration and with longer reaction times, iodine can effect the selective acetolysis of benzyl ether-protected primary hydroxyl groups. All of these reactions proceed in high yield, are easy to carry out and make use of readily available iodine, which is both cheap and easy to handle.

Iodine has been found to be an excellent reagent for converting free sugars into their per-O-acetylated derivatives. Under controlled conditions selective partial acylation or acetolysis can be achieved.
Original languageUndefined
Pages (from-to)11753-11766
Number of pages14
JournalTetrahedron
Volume53
Issue number34
DOIs
Publication statusPublished - 25 Aug 1997

Research Beacons, Institutes and Platforms

  • Manchester Institute of Biotechnology

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