{"title":"Supramolecular assisted O-acylation of carbohydrates†","authors":"Soumyadip Dey , Debabrata Giri , Adrita Nandy , Abhijit Sau","doi":"10.1039/d5gc00499c","DOIUrl":null,"url":null,"abstract":"<div><div>The acylation of hydroxy groups serves as one of the most employed protecting group strategies in carbohydrate chemistry. Here, we present a base-free, supramolecular assisted approach for the <em>O</em>-acylation of carbohydrates under mild conditions, using 18-crown-6 in combination with a catalytic amount of potassium fluoride. This sustainable and useful method successfully converted various functional groups containing carbohydrate hydroxy groups into <em>O</em>-acyl, <em>O</em>-benzoyl, and <em>O</em>-propionyl derivatives with up to 99% yields.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"27 18","pages":"Pages 4995-5000"},"PeriodicalIF":9.3000,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Green Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1463926225002961","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
The acylation of hydroxy groups serves as one of the most employed protecting group strategies in carbohydrate chemistry. Here, we present a base-free, supramolecular assisted approach for the O-acylation of carbohydrates under mild conditions, using 18-crown-6 in combination with a catalytic amount of potassium fluoride. This sustainable and useful method successfully converted various functional groups containing carbohydrate hydroxy groups into O-acyl, O-benzoyl, and O-propionyl derivatives with up to 99% yields.
期刊介绍:
Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.