Investigation on condensing agents for phosphinate ester formation with nucleoside 5′-hydroxyl functions was written by Winqvist, Anna;Stroemberg, Roger. And the article was included in European Journal of Organic Chemistry in 2008.Electric Literature of C17H27F6N7OP2 The following contents are mentioned in the article:
Condensation of a uridine 3′-deoxy-3′-C-methylenephosphinate with thymidine and guanosine derivatives to form methylenephosphinate esters was investigated. A number of different condensing agents were compared, and these include pivaloyl chloride, triisopropylbenzenesulfonyl chloride (TPS-Cl), phosphonium and uronium derivatives, numerous chlorophosphates and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (OXP). The phosphonium derivatives gave slow condensations or oxidative side reactions (hydroxybenzotriazole derivatives) during preactivation of the methylenephosphinate. Pivaloyl chloride gave long coupling times, and competing 5′-O-pivaloylation was detected. TPS-Cl gave rapid condensation but also rapid oxidation of the product. Most chlorophosphates gave competing 5′-O-phosphorylation of the nucleoside component, as well as base phosphorylation. However, 2-chloro-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinane (DMOCP) gave a rather efficient formation of dinucleoside methylenephosphinates at a decent rate. However, O6-protection of guanines could become necessary with this reagent, since upon extended reaction time traces of O6-phosphorylation were detected even with a low concentration (60 mM) of DMOCP (2 equivalent to phosphinate). Bis(2-oxo-3-oxazolidinyl)phosphinic chloride (OXP) can, unlike DMOCP, be used in nearly equimolar amounts to phosphinate. Under such conditions OXP gives virtually quant. condensation at a rate comparable to that of 2 equivalent of DMOCP and with no side reactions detected. Any decomposition of OXP-preactivated phosphinate could also not be detected. Nucleophilic catalysts, more powerful than pyridine (N-methylimidazole, iodide and 4-methoxypyridine), accelerated the reactions with OXP, but preactivation in the absence of the 5′-OH component led to decomposition of the activated phosphinate. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Electric Literature of C17H27F6N7OP2).
((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. Triazoles are important five-member nitrogen heterocycles involved in a wide range of industrial applications such as agrochemicals, corrosion inhibitors, dyes, optical brighteners, as well as biologically active agents.Triazole heterocyclic structures are found to form many weak nonbond interactions with the receptors and enzymes in biological systems.Electric Literature of C17H27F6N7OP2
Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics