{"title":"NFSI-TEMPO Catalysed Stereoselective Synthesis of 2-Deoxyglycosides from Glycals","authors":"Vivek Kumar Sharma, Rima Thakur","doi":"10.1002/adsc.202401450","DOIUrl":null,"url":null,"abstract":"2-deoxyglycosides are prominent constituents of diverse naturally occurring glycans and are known to participate in crucial biological pathways. We herein demonstrate NFSI-TEMPO as an efficient organocatalyst for the formation of 2-deoxy-α-glycosides from glycals. For the first time a catalytic behaviour of NFSI-TEMPO combination has been observed. The reaction conditions have been found suitable for the generation of glycosides from commercial alcohols, amino acid, sterol, phenols and monosaccharide derived alcohols. Broad range of protecting groups on both glycal and glycosyl acceptors as well as alcohols of varied reactivity were found to be compatible for the generation of 2-deoxy-α-glycosides in moderate to good yields. The synthetic potential of the newly established transformation was illustrated by application in trisaccharide synthesis and gram-scale reaction.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"9 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202401450","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
2-deoxyglycosides are prominent constituents of diverse naturally occurring glycans and are known to participate in crucial biological pathways. We herein demonstrate NFSI-TEMPO as an efficient organocatalyst for the formation of 2-deoxy-α-glycosides from glycals. For the first time a catalytic behaviour of NFSI-TEMPO combination has been observed. The reaction conditions have been found suitable for the generation of glycosides from commercial alcohols, amino acid, sterol, phenols and monosaccharide derived alcohols. Broad range of protecting groups on both glycal and glycosyl acceptors as well as alcohols of varied reactivity were found to be compatible for the generation of 2-deoxy-α-glycosides in moderate to good yields. The synthetic potential of the newly established transformation was illustrated by application in trisaccharide synthesis and gram-scale reaction.
期刊介绍：
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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