{"@context":{"@vocab":"https://cir.nii.ac.jp/schema/1.0/","rdfs":"http://www.w3.org/2000/01/rdf-schema#","dc":"http://purl.org/dc/elements/1.1/","dcterms":"http://purl.org/dc/terms/","foaf":"http://xmlns.com/foaf/0.1/","prism":"http://prismstandard.org/namespaces/basic/2.0/","cinii":"http://ci.nii.ac.jp/ns/1.0/","datacite":"https://schema.datacite.org/meta/kernel-4/","ndl":"http://ndl.go.jp/dcndl/terms/","jpcoar":"https://github.com/JPCOAR/schema/blob/master/2.0/"},"@id":"https://cir.nii.ac.jp/crid/1361137044656056320.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1139/v71-076"}},{"identifier":{"@type":"URI","@value":"https://cdnsciencepub.com/doi/pdf/10.1139/v71-076"}}],"dc:title":[{"@value":"Oligoribonucleotide Synthesis. II. Preparation of 2′-<i>O</i>-tetrahydropyranyl Derivatives of Adenosine and Cytidine Necessary for Insertion in Stepwise Synthesis"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:p> The syntheses of N<jats:sup>6</jats:sup>-benzoyl-2′-O-tetrahydropyranyladenosine (2) and N<jats:sup>4</jats:sup>-benzoyl-2′-O-tetrahydropyranylcytidine (11) and their corresponding 5′-O-p-methoxytrityl derivatives, 3 and 12 respectively, are described. Compounds 2, 3, 11, and 12 are the protected derivatives of adenosine and cytidine required for insertion into a new oligoribonucleotide synthesis. Compound 2 was prepared from the known 2′-O-tetrahydropyranyladenosine by perbenzoylation followed by de-O-benzoylation. Compound 11 is prepared from cytidine by the following sequence: orthoacetate protection of the 2′- and 3′-hydroxyls; benzoylation of the 5′- and N<jats:sup>4</jats:sup>-positions; orthoacetate ring opening provided a mixture of the 2′- and 3′-monoacetates from which the major, 3′-O-acetyl-N<jats:sup>4</jats:sup>,5′-O-dibenzoylcytidine (7) was isolated; dihydropyran treatment on the 2′-hydroxyl of 7 and subsequent selective deacylation studies were carried out. Specific de-O-acylation gave 11. </jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1381137044656056192","@type":"Researcher","foaf:name":[{"@value":"Thomas Neilson"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137044656056320","@type":"Researcher","foaf:name":[{"@value":"Eva S. Werstiuk"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00084042"},{"@type":"EISSN","@value":"14803291"}],"prism:publicationName":[{"@value":"Canadian Journal of Chemistry"}],"dc:publisher":[{"@value":"Canadian Science Publishing"}],"prism:publicationDate":"1971-02-01","prism:volume":"49","prism:number":"3","prism:startingPage":"493","prism:endingPage":"499"},"reviewed":"false","dc:rights":["http://www.nrcresearchpress.com/page/about/CorporateTextAndDataMining"],"url":[{"@id":"https://cdnsciencepub.com/doi/pdf/10.1139/v71-076"}],"createdAt":"2006-05-04","modifiedAt":"2025-07-02","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360283694076781184","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Asymmetric Synthesis with Sugar Derivatives. V. The Synthesis of α-Hydroxy Acids on Insoluble Polymer Supports"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1139/v71-076"},{"@type":"CROSSREF","@value":"10.1246/bcsj.47.160_references_DOI_AVFkczhBdk66Yu2tmTc13esrAJ1"}]}