Propylphosphonic anhydride (T3P®): An expedient reagent for organic synthesis

Waghmare, Anirudha A.; Hindupur, Rama Mohan; Pati, Hari N.

doi:10.1134/s2079978014020034

Cited by 50 publications

(39 citation statements)

References 108 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We therefore took steps to improve this by eliminating the use of the toxic acryloyl and methacryloyl chloride and substituting with acrylic and methacrylic acid; both of which will become commercially available from renewable sources. To effect this strategy we introduced propyl phosphonic anhydride (T3P®) 24 to promote ester coupling between terpene alcohols and acrylic acid. This reagent gives an environmentally benign Yields shown are overall yields in two steps (either hydroboration/oxidation or carbonyl reduction), followed by esterification of the resulting alcohol with (meth)acryloyl chloride.…”

Section: Resultsmentioning

confidence: 99%

A facile and green route to terpene derived acrylate and methacrylate monomers and simple free radical polymerisation to yield new renewable polymers and coatings

et al. 2016

View full text Add to dashboard Cite

A note on versions:The version presented here may differ from the published version or from the version of record. If you wish to cite this item you are advised to consult the publisher's version. Please see the repository url above for details on accessing the published version and note that access may require a subscription. We present new acrylic monomers derived directly from abundant naturally available terpenes via a facile, green and catalytic approach. These monomers can be polymerised to create new polymers with a wide range of mechanical properties that positions them ideally for application across the commodity and specialty plastics landscape; from packaging, cosmetic and medical, through to composites and coatings.We demonstrate their utility through formation of novel renewable polymer coatings.

show abstract

Section: Resultsmentioning

confidence: 99%

A facile and green route to terpene derived acrylate and methacrylate monomers and simple free radical polymerisation to yield new renewable polymers and coatings

et al. 2016

View full text Add to dashboard Cite

show abstract

“…These kind of coupling agents are readily available from peptide chemistry, but have to be evaluated for their toxicity. Another commercially available coupling agent for esterification is n-propylphosphonic anhydride (T3P ® ), which is highly versatile, possesses comparably less toxicity and offers mild reaction conditions and workup (Waghmare et al, 2014). While ATRP grafting approaches seem more reasonable for large scale modification of RC membranes the direct esterification approach utilising benign esterification agents appears to offer an easy, least-toxic and reproducible route to small scale and prototyping reactions.…”

Section: Conclusion and Further Propositionsmentioning

confidence: 99%

Surface modification of cellulose membranes

Ziemann¹

2017

Preprint

View full text Add to dashboard Cite

show abstract

“…T3P® is a phosphorous‐containing cyclic anhydride that was introduced by Wissmann and Kleiner as a condensation reagent for peptide synthesis [30] (Figure 2). Unlike other common coupling reagents, T3P® has a low toxicity and allergy profile, as demonstrated by taxicological studies [31,32] . A significant advantage in the use of T3P®, is that the by‐products of the reaction are highly water soluble and can readily be washed away from products with less good water solubility.…”

Section: Introductionmentioning

confidence: 99%

Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid‐Phase Peptide Synthesis

Musaimi

Wisdom²,

Talbiersky³

et al. 2021

ChemistrySelect

View full text Add to dashboard Cite

Amidation is the predominant reaction within the pharmaceutical setting, and it is attracting greater attention due to the increased demand for therapeutic peptides. The high therapeutic efficacy and safety profile of peptides have placed these molecules in prime position within the pharmaceutical arena, which is reflected by these molecules receiving several approvals from various regulatory agencies each year. In this context, the demand for developing efficient strategies for peptide synthesis has also risen. Although propylphosphonic anhydride (T3P®), which has been recently proposed as a green coupling reagent, has shown good performance in solution, it has never been applied to solid‐phase peptide synthesis (SPPS). Here we test the use of T3P® for SPPS. Satisfactory yields were achieved with a mild activation protocol. Various green solvents were tested and proved to be compatible with this coupling reagent. Several commonly used reagents cause allergic reactions or are susceptible to explosion under certain conditions. To overcome these issues, we propose T3P® as a potential alternative coupling reagent in SPPS.

show abstract

Propylphosphonic anhydride (T3P®): An expedient reagent for organic synthesis

Cited by 50 publications

References 108 publications

A facile and green route to terpene derived acrylate and methacrylate monomers and simple free radical polymerisation to yield new renewable polymers and coatings

A facile and green route to terpene derived acrylate and methacrylate monomers and simple free radical polymerisation to yield new renewable polymers and coatings

Surface modification of cellulose membranes

Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid‐Phase Peptide Synthesis

Contact Info

Product

Resources

About