{"title":"NHC-catalysed synthesis of hydroxy methylene-bridged formyl-di-xylofuranose: access to tetrakis and spiro tricyclic xylofuranose.","authors":"Norein Sakander, Rahul Haldar, Debaraj Mukherjee","doi":"10.1039/d5ob00259a","DOIUrl":null,"url":null,"abstract":"<p><p>Herein, the role of <i>N</i>-heterocyclic carbenes (NHC) as a Brønsted base in the transformation of xylofuranose aldehyde has been explored. Furanose aldehyde undergoes intermolecular self-condensation catalyzed by thiazolium-derived carbene, producing hydroxy methylene-bridged formyl-di-xylofuranose retaining the C-4 aldehyde. Furthermore, modification of the hydroxy methylene-linked disaccharide yields spiro[furano-4,5-pyrano[3,2-<i>b</i>]furanose] and oxy-methylene-bridged di-formyl-xylofuranose cyclic tetrasaccharide.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9000,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5ob00259a","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, the role of N-heterocyclic carbenes (NHC) as a Brønsted base in the transformation of xylofuranose aldehyde has been explored. Furanose aldehyde undergoes intermolecular self-condensation catalyzed by thiazolium-derived carbene, producing hydroxy methylene-bridged formyl-di-xylofuranose retaining the C-4 aldehyde. Furthermore, modification of the hydroxy methylene-linked disaccharide yields spiro[furano-4,5-pyrano[3,2-b]furanose] and oxy-methylene-bridged di-formyl-xylofuranose cyclic tetrasaccharide.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.