The goal of this project is to reduce reaction time and byproduct formation for synthesis of protected carbobenzyloxy-L-serine-benzyl ester cyclohexyl H-phosphonate diester (CBZ-L-Ser-PH-cyc) for use towards the synthesis of cyclohexylphosphoserine to serve as a phosphatidylserine (PS) analog. PS is a phospholipid that is located in cellular membrane and participates in cell functions such as apoptosis and nutrient transportation. The starting material, carbobenzyloxy-L-serine-benzyl ester H-phosphonate monoester (CBZ-L-Ser-PH), a white powdery solid, was converted to the target compound CBZ-L-Ser-PH-cyc, an off-yellow oil. The reaction was tracked using <sup>31</sup>P NMR spectroscopy, with the product forming signals consistent with the expected diastereomer formation. The reaction occurred fastest and most selectively with a 1:3 molecular ratio of starting carbobenzyloxy-L-serine-benzyl ester H-phosphonate monoester to pivaloyl chloride. Current work is focused on scaling up the reaction and optimizing purification.

Formation of a protected carbobenzyloxy-L-serine-benzyl ester cyclohexyl H-phosphonate diester towards the synthesis of cyclohexylphosphoserine as a potential phosphatidylserine analog

249th National Meeting (2015)

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