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Regioselective 2′‐Silylation of Purine Ribonucleosides for Phosphoramidite RNA Synthesis

dc.contributor.authorGaffney, Barbara L.
dc.contributor.authorJones, Roger A.
dc.date.accessioned2020-01-13T15:19:10Z
dc.date.available2020-01-13T15:19:10Z
dc.date.issued2001-09
dc.identifier.citationGaffney, Barbara L.; Jones, Roger A. (2001). "Regioselective 2′‐Silylation of Purine Ribonucleosides for Phosphoramidite RNA Synthesis." Current Protocols in Nucleic Acid Chemistry 6(1): 2.8.1-2.8.13.
dc.identifier.issn1934-9270
dc.identifier.issn1934-9289
dc.identifier.urihttps://hdl.handle.net/2027.42/153167
dc.description.abstractThis unit describes high‐yield procedures for protection of purine ribonucleosides based on a reaction that allows concomitant highly regioselective 2′‐silylation and 3′‐phosphitylation to give, in one step, monomers that are ready for H‐phosphonate synthesis. For preparation of phosphoramidites, the H‐phosphonate monoester is cleaved without silyl migration to give intermediates ready for phosphitylation by standard methods.
dc.publisherWiley Periodicals, Inc.
dc.titleRegioselective 2′‐Silylation of Purine Ribonucleosides for Phosphoramidite RNA Synthesis
dc.typeArticle
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelPublic Health
dc.subject.hlbsecondlevelBiological Chemistry
dc.subject.hlbsecondlevelChemical Engineering
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbtoplevelHealth Sciences
dc.subject.hlbtoplevelScience
dc.subject.hlbtoplevelEngineering
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/153167/1/cpnc0208.pdf
dc.identifier.doi10.1002/0471142700.nc0208s06
dc.identifier.sourceCurrent Protocols in Nucleic Acid Chemistry
dc.identifier.citedreferenceChaix, C., Duplaa, A.M., Molko, D., and Téoule, R. 1989. Solid phase synthesis of the 5′‐half of the initiator t‐RNA from B. subtilis. Nucl. Acids Res. 17: 7381 ‐ 7393.
dc.identifier.citedreferenceHakimelahi, G.H., Proba, Z.A., and Ogilvie, K.K. 1982. New catalysts and procedures for the dimethoxytritylation and selective silylation of ribonucleosides. Can. J. Chem. 60: 1106 ‐ 1113.
dc.identifier.citedreferenceOgilvie, K.K., Beaucage, S.L., Schifman, A.L., Theriault, N.Y., and Sadana, K.L. 1978. The synthesis of oligoribonucleotides. II. The use of silyl protecting groups in nucleoside and nucleotide chemistry. VII. Can. J. Chem. 56: 2768 ‐ 2780.
dc.identifier.citedreferenceOgilvie, K.K., Schifman, A.L., and Penney, C.L. 1979. The synthesis of oligoribonucleotides. III. The use of silyl protecting groups in nucleoside and nucleotide chemistry. VIII. Can. J. Chem. 57: 2230 ‐ 2238.
dc.identifier.citedreferenceSingh, K.K., and Nahar, P. 1995. An improved method for the synthesis of N ‐phenoxyacetylribonucleosides. Synth. Commun. 25: 1997 ‐ 2003.
dc.identifier.citedreferenceSinha, N.D., Davis, P., Schultze, L.M., and Upadhya, K. 1995. A simple method for N ‐acylation of adenosine and cytidine nucleosides using carboxylic acids activated in situ with carbonyldiimidazole. Tetrahedron Lett. 36: 9277 ‐ 9280.
dc.identifier.citedreferenceSong, Q., Wang, W., Fischer, A., Zhang, X., Gaffney, B.L., and Jones, R.A. 1999. High yield protection of purine ribonucleosides for phosphoramidite RNA synthesis. Tetrahedron Lett. 40: 4153 ‐ 4156.
dc.identifier.citedreferenceWu, T., Ogilvie, K.K., and Pon, R.T. 1988. N ‐Phenoxyacetylated guanosine and adenosine phosphoramidites in the solid phase synthesis of oligoribonucleotides: Synthesis of a ribozyme sequence. Tetrahedron Lett. 29: 4249 ‐ 4252.
dc.identifier.citedreferenceZemlicka, J. 1963. Reactions of dimethylformamide acetals with some heterocyclic systems. Collect. Czech. Chem. Commun. 28: 1060 ‐ 1062.
dc.identifier.citedreferenceZhang, X., Abad, J.‐L., Huang, Q., Zeng, F., Gaffney, B.L., and Jones, R.A. 1997. High yield protection of purine ribonucleosides for H ‐phosphonate RNA synthesis. Tetrahedron Lett. 38: 7135 ‐ 7138.
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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