Practical synthesis of the anti-HIV drug, PMPA

A multikilogram process to prepare the antiviral agent PMPA is described. 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...

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Bibliographic Details
Published in:Tetrahedron letters 1998-04, Vol.39 (14), p.1853-1856
Main Authors: Schultze, Lisa M., Chapman, Harlan H., Dubree, Nathan J.P., Jones, Robert J., Kent, Kenneth M., Lee, Thomas T., Louie, Michael S., Postich, Michael J., Prisbe, Ernest J., Rohloff, John C., Yu, Richard H.
Format: Article
Language:English
Subjects:
HIV
nucleotide
phosphonate
PMEA
PMPA
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Summary:A multikilogram process to prepare the antiviral agent PMPA is described. 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)00131-2