ChemInform Abstract: CYCLIC COMPOUNDS WITH A FIVE‐COORDINATE PHOSPHORUS ATOM ‐ BIS(O‐TOLYL)PHOSPHINE OXIDE DERIVATIVES

Петров, К. А.; Chauzov, V. A.; Mal'kevich, N. Yu.; Kostrova, S. M.

doi:10.1002/chin.197822241

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“…Di- o -tolylphosphinic Chloride (DtpCl, 11). , Di- o -tolylphosphinic acid (13.5 g) was slowly added to 50 mL of thionyl chloride with cooling in an ice bath. The mixture was refluxed under a CaCl 2 drying tube for 3 h. After removal of excess thionyl chloride by a water aspirator in a hood, the oily residue was fractionally distilled to give 13.55 g (93.4%) of the phosphinic chloride as a colorless oil (bp 158−165 °C/0.1 mmHg) which solidified quickly (lit .…”

Section: Methodsmentioning

confidence: 99%

Organophosphorus and Nitro-Substituted Sulfonate Esters of 1-Hydroxy-7-azabenzotriazole as Highly Efficient Fast-Acting Peptide Coupling Reagents

et al. 2003

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Organophosphorus esters 9, 10, 14, and 15 prepared via reaction of diethyl- and diphenylphosphoryl chloride, di(o-tolyl)phosphinyl chloride, and 2,8-dimethylphenoxaphosphinyl chloride with HOAt are excellent coupling reagents for peptide synthesis which are generally superior to their uronium/guanidinium analogues and HOBt- or HODhbt-derived phosphate ester counterparts in minimizing loss of configuration during segment coupling. The phosphinyl analogues are more shelf-stable than the phosphoryl systems. The new reagents have been tested in segment couplings leading to two tripeptides (20, 21) and a hexapeptide 22. Outstanding utility is also shown for the solid-phase assembly of the ACP decapeptide. Similar results were obtained with the 2- and 4-nitro- and 2,4-dinitrophenylsulfonyl esters derived from HOAt.

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Section: Methodsmentioning

confidence: 99%