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Synthesis of a phosphinate analogue of the anti-tumour phosphate di-ester perifosine via sequential radical processes†
Marios S. Markoulides,Andrew C. Regan
Organic & Biomolecular Chemistry Pub Date : 10/03/2012 00:00:00 , DOI:10.1039/C2OB26395E
Abstract

An efficient synthesis of a phosphinate analogue of the anti-tumour phosphate di-ester perifosine is described (6 steps and 50% overall yield). The two phosphorus窶田arbon bonds in the perifosine analogue were prepared by sequential double radical hydrophosphinylation processes. This is the first example of a phosphinate analogue of perifosine, designed to be resistant to hydrolysis by phospholipid-metabolizing enzymes.

Graphical abstract: Synthesis of a phosphinate analogue of the anti-tumour phosphate di-ester perifosine via sequential radical processes
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