Lisa M Schultze

Practical synthesis of the anti-HIV drug, PMPA

Abstract The anti-HIV nucleotide analogue PMPA can be prepared on a kilogram-scale by a three step sequence: i) condensation of adenine with ( R )-propylene carbonate, ii) alkylation of the resulting ( R )-9-(2-hydroxypropyl)adenine with diethyl p -toluenesulfonyloxymethanephosphonate using lithium tert -butoxide and iii) cleavage of the phosphonate ester functionalities with bromotrimethylsilane.

A simple method for N-acylation of adenosine and cytidine nucleosides using carboxylic acids activated In-Situ with carbonyldiimidazole

Summary Carboxylic acids are activated with 1.1′-carbonyldiimidazole in acetonitrile to form N-acylimidazoles which are then treated with per-trimethylsilyl ethers of nucleosides adenosine or cytidine at ambient temperature to generate exclusively N-acylated-Adenosine or N-acylated-Cytidine derivatives.