51649-25-3

Upstream product

• 324753-14-2 S-(diphenylphosphinoyl)methyl ethanethioate 
• 4559-70-0 Diphenylphosphine oxide 
• 884-74-2 (diphenylphosphinoyl)methanol 
• 1806-49-1 diphenyl(chloromethyl)phosphine oxide 
• 324753-16-4 (diphenylphosphanyl)methanethiol 

Downstream Products

• 613688-05-4 diphenylphosphaneylmethanethiol borane complex 
• 80738-09-6 2-(1-acetoxyethyl)-3,5-dimethyl-6-diphenylphosphinyl-2,5,6-trihydrothiopyran 
• 80738-08-5 3,5-dimethyl-6-diphenylphosphinyl-2-trimethylsilyl-2,5,6-trihydrothiopyran 
• 80738-04-1 2-(Diphenyl-phosphinoylmethylsulfanyl)-1-phenyl-ethanone 

Relevant academic research and scientific papers

Reduction of Tertiary Phosphine Oxides by BH 3 Assisted by Neighboring Activating Groups

Tertiary sulfanylphosphine and aminoalkylphosphine oxides can be easily converted into the corresponding tertiary sulfanylphosphine- and aminoalkylphosphine-boranes, respectively, through the facile P=O bond reduction by borane complexes. The easy reduction of the strong P=O bond by BH 3, a mild reducing agent, has been achieved through an intramolecular P=O - B complexation directed by proximal SH or NH activating groups located at the α- or β-position to the P=O bond. A generalized reduction mechanism has been proposed.

Acidic and basic deprotection strategies of borane-protected phosphinothioesters for the traceless Staudinger ligation

The traceless Staudinger ligation has recently found various applications in the field of peptide synthesis and modification, including immobilization and cyclization strategies. In this report, we utilize the traceless Staudinger ligation in the formation of amide bonds, which allows the acquisition of acylated aminosugars and peptides as well as the cyclization of peptides. A key element in these synthetic procedures is the use of a borane-protected phosphinomethanethiol, which is demonstrated to be prone towards oxidation in its unprotected form, during the synthesis of phosphinothioesters. In combination with acidic and basic deprotection strategies for the borane-protected phosphinothioesters, amide bonds can be formed in the presence of azides in moderate to good overall yields.

Preparation and reactivity of chalcogenyl phosphonates and phosphane oxides

The preparation of new bis[(diphenylphosphinoyl)methyl] sulfides, selenides, and tellurides is described by the reaction of (diphenylphosphinoyl) methyl p-toluenesulfonate with sodium chalcogenides. The title compounds are subjected to Horner-Wittig-type