Diesters synthesis

P. Potier, A. Bouchu, G. Descotes, and Y. Queneau, Lipase-catalysed selective synthesis of sucrose mixed diesters, Synthesis (2001) 458-462. 

The oxidopicolyl group increases the rate and efficiency of internucleotide phospho-diester synthesis. It is cleaved with piperidine. ... 

Dealing with the sulphosuccinate diester synthesis, the esterification procedure is performed very similar to that described above for monoesters but the feed of hydroxyl-bearing material (generally Ce-u alcohols) should be twice more with respect to maleic anhydride. The first step is performed under a gradually increasing temperature to 120-150 °C and with continuous vacuum distillation of water from esterification. At that step esterification catalyst may be used, such as /7-toluenesulphonic acid or ABSA. The sulphonation with sodium bisulphite proceeds as described above. A representative example of diesters is sodium bis(2-ethylhexyl) sulphosuccinate known as Aerosol OT of the formula ... 

Notice that the actual phosphodiester bond formation did not involve the reaction of a phosphorochloridate with the 5 -hydroxyl of the nucleoside. This approach has been seldom used for diester synthesis as these reactions tend to be sluggish and can be complicated by comparison with other methods. More favorable is the reaction of a nucleoside phosphorochloridite with a second molecule of nucleoside, as shall be discussed shortly. Alternatively, phosphodiester formation may be accomplished via in situ activation of a nucleotide with a condensing agent. Some of these reagents are described below. 

General Synthesis and Reactions of Esters Synthesis of Diesters Synthesis of Hydroxy-esters Synthesis of Keto-esters Synthesis of Unsaturated Esters Synthesis of Aromatic Esters Synthesis of Thioesters Synthesis of Vinylogous Esters... 

Stawinski, J Thelin, M, and Zain, R (1989) Nucleoside H-phosphonates. X. Studies on nucleoside hydrogenphosphonothioate diester synthesis. Tetrahedron Lett 30,2157-2160. 

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