New Efficient Method of Oxidation of Poly(alkylene H-phosphonate)s: A Promising Route to Novel co-Polyphosphoesters

Abstract

A novel method of oxidation of poly(alkylene Hphosphonate)s is presented here. Trichloroisocyanuric acid is used for the first time as a chlorination agent of poly(alkylene Hphosphonate)s. Poly(oxyethylene chlorophosphate) was obtained in quantitative yield at room temperature in 1 h from poly(oxyethylene H-phosphonate) and trichloroisocyanuric acid. Poly(alkylene chlorophosphate)s have been used as an efficient polymer carriers of low molecular biologically active substances bearing hydroxyl or amino groups. Using different molar ratio between trichloroisocyanuric acid and poly(alkylene H-phosphonate) can control the degree of oxidation, and novel co-polyphosphoesters with new properties can be obtained.

Design, Synthesis and Actual Applications of the Polymers Containing Acidic P–OH Fragments: Part 1. Polyphosphodiesters

“…To date, multiple approaches to polyphosphodiesters have been developed. The most evident synthetic pathway is based on the interaction of phosphoric acid with diols reviewed by Penczek et al in 2015 [ 1 ] or on transesterification of dialkyl (or diaryl) phosphonates followed by oxidation of P–H bonds [ 23 , 24 , 25 , 26 , 27 , 28 , 29 ]. Ring-opening polymerization (ROP) of strained cyclic phosphonates (containing P–H bonds) and phosphates, followed by post-modification (oxidation or hydrolysis/hydrolytic thermolysis, respectively) is another efficient pathway to polyphosphodiesters [ 30 , 31 ].…”

A Library of Well-Defined and Water-Soluble Poly(alkyl phosphonate)s with Adjustable Hydrolysis

“…Currently, some researchers are interested in poly­(phosphate)­s and poly­(phosphoamidate)­s. − ,− However, backbiting reactions during the polymerization have been reported due to the potentially cleavable side chains (ester or amide).…”

Synthesis of Phosphoester Compounds Using Lactic Acid for Encapsulation of Paclitaxel

“…The structure of alkyl di(MePEG-lactate) phosphates were elucidated by means of 1 H NMR spectroscopy ( Figure 6). The multiplet at δ=4.28-4.36 ppm is characteristic for −OCHH 2 protons (21). Signals at δ=3.62-3.74 ppm can be assigned to protons in the repeating unit of PEG350.…”

“…Phosphorus-based polymers with alkyl side chains introduced have been studied and they are actively investigated for pharmaceutical and biomedical applications such as carriers of drug (13)(14)(15)(16) and genes (17)(18)(19)(20). Although promising compounds were reported as drug carriers capable of regulating solubility and hydrolytic stability, their degradability has not been discussed (21). The lack of degradability of drug carriers causes a decrease in drug efficacy due to difficulty in releasing the drug when delivered to the target site.…”