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. 1991 Nov 11;19(21):5965–5971. doi: 10.1093/nar/19.21.5965

A simple procedure for the preparation of protected 2'-O-methyl or 2'-O-ethyl ribonucleoside-3'-O-phosphoramidites.

E Wagner 1, B Oberhauser 1, A Holzner 1, H Brunar 1, G Issakides 1, G Schaffner 1, M Cotten 1, M Knollmüller 1, C R Noe 1
PMCID: PMC329054  PMID: 1945882

Abstract

Protected 2'-O-methyl and 2'-O-ethyl ribonucleoside-3'-O-phosphoramidites were prepared via alkylation of the ribonucleosides at an early stage in the synthesis. Utilizing a strategy of minimal protection, the alkylation was performed with unprotected cytidine and adenosine, or with O6-protected guanosine and N3,5'-O-protected uridine using methyl or ethyl iodide and sodium hydride. In subsequent steps, the introduction of standard protective groups for oligonucleotide synthesis and the concomitant separation from 3'-O-alkylated isomers was accomplished. A modification of the phosphitylation procedure permitted facile isolation of the desired phosphoramidites which show high coupling efficiencies in oligomer assembly.

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Selected References

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