Ring opening of cyclopropylmethylidene with trimethylaluminum: Synthesis of 1-cyclopropylethyl ether as an acid labile protecting group for hydroxyl Protection and carbohydrate synthesis
{"title":"Ring opening of cyclopropylmethylidene with trimethylaluminum: Synthesis of 1-cyclopropylethyl ether as an acid labile protecting group for hydroxyl Protection and carbohydrate synthesis","authors":"Madhav Poudel , Zainab Bustani , Xiaohua Li , Jianglong Zhu","doi":"10.1080/07328303.2025.2471354","DOIUrl":null,"url":null,"abstract":"<div><div>The 4,6-<em>O</em>-cyclopropylmethylidene (CPMD) moiety of a methyl α-glucoside derivative can be regioselectively opened by trimethylaluminum to afford a corresponding 1-cyclopropylethyl (CPE) ether at C4 and a free alcohol at C6. This 1-CPE ether was found to be an acid-labile hydroxyl protecting group and can be readily cleaved using 10% trifluoracetic acid in dichloromethane at room temperature. The utilization of 1-CPE ether as a hydroxyl protecting group has been demonstrated in the efficient synthesis of a trisaccharide.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"44 1","pages":"Pages 81-93"},"PeriodicalIF":2.2000,"publicationDate":"2025-03-24","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/S0732830325000059","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
The 4,6-O-cyclopropylmethylidene (CPMD) moiety of a methyl α-glucoside derivative can be regioselectively opened by trimethylaluminum to afford a corresponding 1-cyclopropylethyl (CPE) ether at C4 and a free alcohol at C6. This 1-CPE ether was found to be an acid-labile hydroxyl protecting group and can be readily cleaved using 10% trifluoracetic acid in dichloromethane at room temperature. The utilization of 1-CPE ether as a hydroxyl protecting group has been demonstrated in the efficient synthesis of a trisaccharide.
甲基α-葡萄糖苷衍生物的4,6- o -环丙基甲基（CPMD）部分可以被三甲基铝选择性地打开，在C4上得到相应的1-环丙基乙基（CPE）醚和在C6上得到游离醇。该1-CPE醚被发现是一种酸不稳定的羟基保护基团，在室温下用10%的三氟乙酸在二氯甲烷中很容易裂解。利用1-CPE醚作为羟基保护基团，有效合成了一种三糖。
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.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
