Use of Ferric Chloride in Carbohydrate Reactions.1Iv. Acetolysis of Benzyl Ethers of Sugars
- 1 September 1986
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 5 (3) , 437-444
- https://doi.org/10.1080/07328308608058847
Abstract
Acetolysis of benzyl ethers of sugars has been carried out with anhydrous ferric chloride in acetic anhydride. By employing this reagent, benzyl ether groups variously placed in sugars or in their glycosides could be removed with ease and replaced by acetyl groups. By controlled acetolysis, preferential removal of certain benzyl groups was possible. The results show that in D-glucose the relative ease of removal of benzyl ether groups by acetolysis follows the order C-6 > C-4 > C-3 > C-2 and that the rate of acetolysis is 6-O-Bn : 3-O-Bn : 2-O-Bn = 125 : 24 : 1. The corresponding methyl ethers were very sluggish towards acetolysis.This publication has 11 references indexed in Scilit:
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