184834-31-9Relevant articles and documents
Resolution of a citric acid derivative: Synthesis of (R)-(-)-homocitric acid-γ-lactone
Ancliff, Rachael A.,Russell, Andrew T.,Sanderson, Adam J.
, p. 3379 - 3382 (1997)
Both the (R) and (S) enantiomers of the citric acid derivative 1 have been obtained in ≤90% ee via resolution of the racemate by fractional crystallisation of the (S) and (R)-α-methylbenzylamine salts respectively. The stereochemistry of (R)-1 has been assigned by its conversion to (R)-(-)- homocitric acid utilising an Amdt-Eistert homologation followed by acid eatalysed deprotection.
The design and synthesis of nucleoside triphosphate isosteres as potential inhibitors of HIV reverse transcriptase
Weaver, Richard,Gilbert, Ian H.
, p. 5537 - 5562 (2007/10/03)
We describe the synthesis of a variety of lipophilic isosteres of nucleoside triphosphates as potential anti-HIV agents. The citrate molecule proved to be a good mimic of triphosphate by modelling in terms of charge and spatial distribution. Several lipophile derivatives of citrate were conjugated to the precedented anti-HIV nucleoside d4T via ester and amide linkages. A novel synthesis of 5'-amino-d4T is included. Intramolecular rearrangement of several amide-linked isosteres are also reported, along with an alternative synthetic strategy to the desired amide-linked isosteres.