Nucleosidic Phosphoramidite Synthesis via Phosphitylation: Activator Selection and Process Development
Organic Process Research & Development2005Vol. 9(6), pp. 730–737
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Chaoyu Xie, Michael A. Staszak, John T. Quatroche, Christa D. Sturgill, Vien V. Khau, Michael J. Martinelli
Abstract
Nucleosidic phosphoramidites are key building blocks for the automated, solid supported syntheses of oligonucleotide-based drugs. A safe, industrially viable process for preparing nucleosidic phosphoramidites 5-Me-MOE-U and MOE-A has been developed and utilized on multikilogram scales. The optimization of this process is described in detail. Emphasis is placed on the search for activators to replace the hazardous 1H-tetrazole, the development of an extractive workup, and the advancement of a precipitation method to avoid both chromatographic purification and product foaming issues.
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