Bibliographic Details
| Title: |
Solid-Phase Synthesis of Dinucleoside and Nucleoside-Carbohydrate Phosphodiesters and Thiophosphodiesters. |
| 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] |
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| Database: |
Engineering Source |
