13685-36-4

Upstream product

• 15948-60-4 bis(4-chlorophenyl)phosphine oxide 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 1983-26-2 chloromethylphosphonic dichloride 
• 67260-92-8 [Bis-(4-chloro-phenyl)-phosphinoyl]-methanol 

Downstream Products

• 106649-44-9 C₁₉H₁₄Cl₂NO₄P 
• 866363-66-8 thioacetic acid S-{[di-(4-chlorophenyl)phosphanyl oxide]methyl}ester 
• 866363-67-9 4-carboxythiobutyric acid S-{[di-(4-chlorophenyl)phosphanyl oxide]methyl}ester 
• 866363-68-0 4-carboxythiobutyric acid S-{[di-(4-chlorophenyl)phosphanyl]methyl}ester 
• 922517-76-8 thioacetic acid S-{[bis-(4-chloro-phenyl)-phosphanyl]-methyl} ester 
• 1028206-14-5 [bis-(4-chloro-phenyl)-phosphanyl]-methanethiol 

Relevant academic research and scientific papers

Staudinger ligation of peptides at non-glycyl residues

The Staudinger ligation provides a means to form an amide bond between a phosphinothioester and azide. This reaction holds promise for the ligation of peptides en route to the total chemical synthesis of proteins. (Diphenylphosphino)methanethiol is the mo

On the preparation of carbohydrate-protein conjugates using the traceless Staudinger ligation

The nature of a linker used for preparing glycoconjugate vaccines is of utmost importance as it may lead to immunogenic biomolecules. We report the conjugation of carbohydrate haptens to protein carriers leading to potential vaccines using the traceless Staudinger ligation. The ligation relies on the selective transfer of a phosphane substituent to an azide to form a native amide bond in the final product upon release of an oxidized phosphane byproduct. We designed new phosphinofunctionalized cross-linkers suitable for protein carrier derivatization. We evaluated their utility in preparing conjugates using both synthetic and purified bacterial carbohydrates. The use of a borane-protected phosphane which is deprotected at the time of the ligation reaction led to the best results observed thus far in terms of stability toward oxidation and reactivity.

The effect of the phosphoryl group on the rate and mechanism of SN-substitution at the saturated carbon atoms

The reactivity of diarylphosphine oxides RR'P(O)CH2X with p-O2NC6H4ONa in DMF have been studied.The reaction rate increases with the electrodrawing properties of the substituents on R and R' in the following way: p-Me2NC6H4 2 reaction rate of diphenylphosphine oxides has been investigated.The reactivity increases as follows Cl I Br OTs.A reaction mechanism is suggested.