Synthesis And Hydrolytic Properties Of Thymidine P-Boranomonophosphate

Zhihong Xu,Zinaida A. Sergueeva,Barbara Ramsay Shaw

Tetrahedron Letters（2011）

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摘要

Detailed synthetic procedures of thymidine 5′-O-(P-borano)monophosphate (TMPB) via an H-phosphonate approach are reported. The hydrolytic properties of TMPB in pH 1.8 and 6.76 buffers at 22 or 37°C were studied using LC–MS. One nucleoside product, thymidine, was observed, supporting cleavage at the P–O ester bond to release nucleoside and boranophosphate (O3P-BH3−3). Higher temperatures and acidic conditions increase the hydrolysis rates.

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关键词

Thymidine 5′-P-boranomonophosphate,Boranation,H-phosphonate,Boron-modified nucleosides,LC–MS,Stability

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