{"title":"Chemoselective acetonation and one-pot glycosylation/acetylation of free sugars under ultrasonic green energy source","authors":"Nitin Kumar , Ankit Yadav , Saurabh Saini , Sudhir Kashyap","doi":"10.1080/07328303.2025.2527571","DOIUrl":null,"url":null,"abstract":"<div><div>We report a convenient and highly efficient protocol for the acetonation of free sugars, enabling <em>cis-O-</em>isopropylidene saccharide derivatives under ultrasonic irradiation at ambient temperature. Triflic acid (TfOH) in acetone is identified as a mild and effective reagent for the chemoselective <em>O</em>-isopropylidenation of polyhydroxy compounds comprising aldo/keto-hexoses or aldo-pentoses. The synthetic utility of this approach was demonstrated through the preparation of various <em>O</em>-isopropylidene-protected sugar derivatives, which serve as key chiral intermediates for assembling important carbohydrate scaffolds and glycoconjugates. The use of ultrasonic irradiation as an environmentally benign energy source highlights the potential for this method to make a significant contribution to synthetic organic chemistry.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"44 4","pages":"Pages 160-178"},"PeriodicalIF":2.2000,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Carbohydrate Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0732830325000126","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
We report a convenient and highly efficient protocol for the acetonation of free sugars, enabling cis-O-isopropylidene saccharide derivatives under ultrasonic irradiation at ambient temperature. Triflic acid (TfOH) in acetone is identified as a mild and effective reagent for the chemoselective O-isopropylidenation of polyhydroxy compounds comprising aldo/keto-hexoses or aldo-pentoses. The synthetic utility of this approach was demonstrated through the preparation of various O-isopropylidene-protected sugar derivatives, which serve as key chiral intermediates for assembling important carbohydrate scaffolds and glycoconjugates. The use of ultrasonic irradiation as an environmentally benign energy source highlights the potential for this method to make a significant contribution to synthetic organic chemistry.
我们报道了一种方便和高效的游离糖丙酮化方法,使顺- o -异丙基糖衍生物在室温下的超声照射下成为可能。丙酮中的三羧酸(TfOH)是一种温和而有效的化学选择性o-异丙基化试剂,用于多羟基化合物的化学选择性o-异丙基化,包括醛酮己糖或醛戊糖。通过制备各种o -异丙烯保护的糖衍生物,证明了该方法的合成实用性,这些糖衍生物是组装重要碳水化合物支架和糖缀合物的关键手性中间体。超声波辐射作为一种环境友好的能源,突出了这种方法对合成有机化学做出重大贡献的潜力。
期刊介绍:
The Journal of Carbohydrate Chemistry serves as an international forum for research advances involving the chemistry and biology of carbohydrates. The following aspects are considered to fall within the scope of this journal:
-novel synthetic methods involving carbohydrates, oligosaccharides, and glycoconjugates-
the use of chemical methods to address aspects of glycobiology-
spectroscopic and crystallographic structure studies of carbohydrates-
computational and molecular modeling studies-
physicochemical studies involving carbohydrates and the chemistry and biochemistry of carbohydrate polymers.