Solid-Phase Synthesis of Dinucleoside and Nucleoside-Carbohydrate Phosphodiesters and Thiophosphodiesters.
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| Title: | Solid-Phase Synthesis of Dinucleoside and Nucleoside-Carbohydrate Phosphodiesters and Thiophosphodiesters. |
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| Authors: | Ahmadibeni, Yousef1, Parang, Keykavous1 kparang@uri.edu |
| Source: | Journal of Organic Chemistry. 8/18/2006, Vol. 71 Issue 17, p6693-6696. 4p. |
| Subjects: | Nucleosides, Polymers, Carbohydrates, Oxidation, Chemical reactions, Chemistry |
| Abstract: | Unprotected nucleosides (ROH) were reacted with two polymers bound to N,N-diisopropylamino-1,3,2-oxathiaphospholane in the presence of ¹H-terazole. Oxidation with tert-butyl hydroperoxide or sulfurization with Beaucage's reagent, followed by the 1,3,2-oxathiaphospholane ring opening with unprotected nucleosides or carbohydrates (R′OH) in the presence of DBU, afforded nucleoside-(5′-5′)-nucleoside or nucleoside-carbohydrate phosphodiester and thiophosphodiester derivatives through the elimination of polymer-bound ethylene episulfide. This strategy offers the advantages of facile isolation of final products and monosubstitution of unprotected nucleosides and carbohydrates. [ABSTRACT FROM AUTHOR] |
| Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
| Database: | Engineering Source |
| FullText | Text: Availability: 0 |
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| Header | DbId: egs DbLabel: Engineering Source An: 22211092 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: Solid-Phase Synthesis of Dinucleoside and Nucleoside-Carbohydrate Phosphodiesters and Thiophosphodiesters. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Ahmadibeni%2C+Yousef%22">Ahmadibeni, Yousef</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Parang%2C+Keykavous%22">Parang, Keykavous</searchLink><relatesTo>1</relatesTo><i> kparang@uri.edu</i> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 8/18/2006, Vol. 71 Issue 17, p6693-6696. 4p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Nucleosides%22">Nucleosides</searchLink><br /><searchLink fieldCode="DE" term="%22Polymers%22">Polymers</searchLink><br /><searchLink fieldCode="DE" term="%22Carbohydrates%22">Carbohydrates</searchLink><br /><searchLink fieldCode="DE" term="%22Oxidation%22">Oxidation</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+reactions%22">Chemical reactions</searchLink><br /><searchLink fieldCode="DE" term="%22Chemistry%22">Chemistry</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: Unprotected nucleosides (ROH) were reacted with two polymers bound to N,N-diisopropylamino-1,3,2-oxathiaphospholane in the presence of ¹H-terazole. Oxidation with tert-butyl hydroperoxide or sulfurization with Beaucage's reagent, followed by the 1,3,2-oxathiaphospholane ring opening with unprotected nucleosides or carbohydrates (R′OH) in the presence of DBU, afforded nucleoside-(5′-5′)-nucleoside or nucleoside-carbohydrate phosphodiester and thiophosphodiester derivatives through the elimination of polymer-bound ethylene episulfide. This strategy offers the advantages of facile isolation of final products and monosubstitution of unprotected nucleosides and carbohydrates. [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.) |
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| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1021/jo0611115 Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 4 StartPage: 6693 Subjects: – SubjectFull: Nucleosides Type: general – SubjectFull: Polymers Type: general – SubjectFull: Carbohydrates Type: general – SubjectFull: Oxidation Type: general – SubjectFull: Chemical reactions Type: general – SubjectFull: Chemistry Type: general Titles: – TitleFull: Solid-Phase Synthesis of Dinucleoside and Nucleoside-Carbohydrate Phosphodiesters and Thiophosphodiesters. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Ahmadibeni, Yousef – PersonEntity: Name: NameFull: Parang, Keykavous IsPartOfRelationships: – BibEntity: Dates: – D: 18 M: 08 Text: 8/18/2006 Type: published Y: 2006 Identifiers: – Type: issn-print Value: 00223263 Numbering: – Type: volume Value: 71 – Type: issue Value: 17 Titles: – TitleFull: Journal of Organic Chemistry Type: main |
| ResultId | 1 |
