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42.16.1.1.4.2.2 Variation 2: Activation by Conversion into Phosphorodichloridates

DOI: 10.1055/sos-SD-042-00920

McKenna, C. E.; Kashemirov, B. A.; Błażewska, K. M.Science of Synthesis, (200942795.

Nucleoside 5-diphosphates 45 can be synthesized from the corresponding phosphorodichloridates 44 (Scheme 15), obtained by phosphorylation of the nucleosides 43 with phosphoryl chloride (see Section 42.16.1.1.2.1). However, this approach can be complicated by side reactions such as the formation of the nucleoside triphosphate via a cyclic triphosphate intermediate.[‌48‌,‌53‌] The ratio between the di- and triphosphate product depends on the amount of tributylamine that is used in the second step of this one-pot reaction.

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