Jianhong Zhang , Tetsuo Koyama , Takahiko Matsushita , Ken Hatano , Koji Matsuoka
{"title":"Use of an oxazolidinone derivative of a sialyl thioglycoside as a useful glycosyl donor for α-favorable glycosidation with simple alcohols","authors":"Jianhong Zhang , Tetsuo Koyama , Takahiko Matsushita , Ken Hatano , Koji Matsuoka","doi":"10.1016/j.tetlet.2024.155189","DOIUrl":null,"url":null,"abstract":"<div><p>An efficient synthesis of lauryl thioglycoside of oxazolidinones derived from <em>N</em>-acetyl neuraminic acid was accomplished from a known thioglycoside of Neu5Ac. The <em>O</em>-glycosidation reactivities of the oxazolidinones were evaluated by means of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and <em>N</em>-iodosuccinimide (NIS) as a combined-mediator system. The glycosidation reaction of the lauryl thioglycoside with simple alcohols proceeded smoothly to yield the corresponding α-glycosides in good yields after isolation. The results suggested that the glycosylation reaction using the oxazolidinone derivative of sialic acid has excellent α-stereoselectivity and enables easy isolation of the desired product from the reaction mixture.</p></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2024-07-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0040403924002843/pdfft?md5=0b656e2efd5e3b124e4fd9c962bb596a&pid=1-s2.0-S0040403924002843-main.pdf","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924002843","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
An efficient synthesis of lauryl thioglycoside of oxazolidinones derived from N-acetyl neuraminic acid was accomplished from a known thioglycoside of Neu5Ac. The O-glycosidation reactivities of the oxazolidinones were evaluated by means of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and N-iodosuccinimide (NIS) as a combined-mediator system. The glycosidation reaction of the lauryl thioglycoside with simple alcohols proceeded smoothly to yield the corresponding α-glycosides in good yields after isolation. The results suggested that the glycosylation reaction using the oxazolidinone derivative of sialic acid has excellent α-stereoselectivity and enables easy isolation of the desired product from the reaction mixture.
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.