389128-28-3

Usage

Uses

Used in Pharmaceutical Industry:
5'(S)-(uracil-1-yl)-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester is used as an intermediate in the synthesis of (2R-cis)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]-2,4(1H,3H)-pyrimidinedione, which is an impurity of Lamivudine (L172500). Lamivudine is an important antiviral drug used in the treatment of HIV and chronic hepatitis B.
Additionally, (2R-cis)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]-2,4(1H,3H)-pyrimidinedione is being further studied to determine its potential as an anti-HIV agent. The development of 5'(S)-(uracil-1-yl)-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester could lead to new therapeutic options for patients suffering from HIV, offering alternative treatment strategies and potentially improving the effectiveness of current antiviral therapies.

Upstream product

• 147027-09-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate 

Downstream Products

• 389128-32-9 5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-2'(R)-dibenzyl-oxyphosphoryloxymethyl-1',3'-oxathiolane 
• 389128-30-7 5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester 
• 389128-29-4 5'(S)-[O⁴-(2,4,6-triisopropylbenzenesulfonyl)uracil-1-yl]-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester 

Relevant academic research and scientific papers

Synthesis of haptens for the development of immunoassays for the monitoring of intracellular anti-HIV nucleosides and nucleotides

A series of nine modified dideoxynucleosides and dideoxynucleotides has been synthesized for preparing antigenic conjugates with keyhole lympet haemocyanin in order to produce specific antibodies, and develop immunoassays. Derivatives of ddI, ddA, d4T, 3TC, and the corresponding 5′-O-monophosphates were designed incorporating an amino spacer at the base for conjugation with the proteinic antigenic carrier.