{"title":"Synthesis of 2-hydroxy analogues of castanospermine, 1-epi-castanospermine and their iminooctitols from sugar-derived lactam","authors":"Nagaraja Ingaladal , Ravi S. Lankalapalli","doi":"10.1016/j.carres.2025.109385","DOIUrl":null,"url":null,"abstract":"<div><div>The synthesis of 2-hydroxy analogues of castanospermine from two new iminooctitols via Mitsunobu cyclization is described. The iminooctitols were derived from the dihydroxylation of an allyl alcohol intermediate, obtained by adding vinylmagnesium bromide to the C6-aldehyde of a protected 1-deoxynojirimycin. An orthogonally protected hemiacetal with silyl group at the C6-hydroxy position and remaining as benzyl ethers, synthesized in four steps from <span>d</span>-glucose, served as a building block in the synthesis of the 1-deoxynojirimycin intermediate.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109385"},"PeriodicalIF":2.4000,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Carbohydrate Research","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0008621525000114","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
The synthesis of 2-hydroxy analogues of castanospermine from two new iminooctitols via Mitsunobu cyclization is described. The iminooctitols were derived from the dihydroxylation of an allyl alcohol intermediate, obtained by adding vinylmagnesium bromide to the C6-aldehyde of a protected 1-deoxynojirimycin. An orthogonally protected hemiacetal with silyl group at the C6-hydroxy position and remaining as benzyl ethers, synthesized in four steps from d-glucose, served as a building block in the synthesis of the 1-deoxynojirimycin intermediate.
期刊介绍：
Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects.
Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence.
Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".
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