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Please login to access the full content or check if you have access via42.16.1.1.4.2.2 Variation 2: Activation by Conversion into Phosphorodichloridates
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McKenna, C. E.; Kashemirov, B. A.; Błażewska, K. M., Science of Synthesis, (2009) 42, 795.
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.
Meeeee 88 Meeeeeeee ee Meeeeeeeee 8′-Meeeeeeeeeee eee 8′-Meeeeeeeeeeeeeeeeeeeee[88]
Meeeeeeeeeee Meeeeeeee
Meeeeeeeee 8′-Meeeeeeeeeee 88; Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeeeeeeeeeeeeeeee eeeeeeeeeee eee eeeeeeeeee eee eee eeeee eeeee ee eee eeee, eeee, eee eeeeeeeeeee eee eeeeeeeeeeeeeeee eeeeeee.
Meeeeeeeeee eeeeeeeeee 88 (8 eeee) eee eeeeeeeee ee M(M)(MMe)8 (eeeee eeee 88-Å eeeeeeeee eeeeee; 8 eM), eee eee eeeeeee eee eeeeeee ee ee eeeee eeeee, eeee eeeeee ee 8°M. Mee 8,8-M,M,M′,M′-eeeeeeeeeeeeeeeeeeeeee-8,8-eeeeeee (Meeeee-Meeeee; 8.88 e, 8.8 eeee) eee eeeee, eeeeeeee 8 eee eeeee ee MMMe8 (8.88 e, 8.8 eeee). Mee eeeeeee eee eeeeeee eee eeeeeee eeeee ee 8–8°M eeee Me8M (8.8 eM, 8.88 eeee) eee eeeee eeeeeeee ee e 8.8 M eeee ee Me8MM+M8MM8– ee MMM (88 eM, 8 eeee). Meeee 8–8 eee, eee eeeeeee eee eeeeee eeee e eeee 8.8 M eeee ee Me8MM+MMM8– ee M8M (88 eM, eM 8.8) eee eeeeeee ee 8–8°M eee eeeeeee eee. Mee eeee eee eeeeeee ee eeeee ee eeeee eeeeeeee eee eeee eeee ee eeeee eee 8 e. M(M)(MMe)8 eee eeeeeeeee eeee e-MeMMe, eee eee eeeeeee eeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eeeeeeeeeee ee eeee e eeeeee, eeeeeeeee eee; eeeee: eee eeeeeeee.
References
[48] | Me-Meeee, M.; Me, M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[53] | Meeeee, M. M.; Meeee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |