184834-31-9

Usage

Chemical class

Dioxolanes

Mono methyl ester of

1,3-dioxolane-4,4-diacetic acid

Use

Synthetic intermediate in the production of pharmaceuticals and agrochemicals

Potential

Building block in organic synthesis due to unique structure and reactivity

Applications

Pharmaceutical industry, synthesis of various drugs and active pharmaceutical ingredients

Safety precautions

Proper handling and safety measures should be taken to ensure the safety of workers and the environment

Upstream product

• 67-56-1 methanol 
• 4767-12-8 4,4-(5-oxo-1,3-dioxolane)diacetic acid anhydride 
• 77-92-9 citric acid 
• 144-16-1 5-oxo-1,3-dioxolan-4-ylidenedi(acetic acid) 

Downstream Products

• 199341-50-9 ((S)-4-Methoxycarbonylmethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid 
• 199341-35-0 [(4R)-(+)-4-(2-methoxy-2-oxoethyl)-5-oxo-1,3-dioxolan-4-yl]acetic acid 
• 199341-36-1 C₈H₁₀O₇*C₈H₁₁N 
• 173934-26-4 (R)-(-)-homocitric acid lactone 
• 53798-97-3 3-hydroxy-5-methoxy-3-(methoxycarbonyl)-5-oxopentanoic acid 

Relevant academic research and scientific papers

Resolution of a citric acid derivative: Synthesis of (R)-(-)-homocitric acid-γ-lactone

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.

An improved synthesis of trisodium (U)-homocitrate from citric acid

A method of synthesis of trisodium (R)-homocitrate starting from citric acid is reported. The procedure affords the final product of high optical purity with satisfactory yield.

The design and synthesis of nucleoside triphosphate isosteres as potential inhibitors of HIV reverse transcriptase

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.

Isosteres of nucleoside triphosphates

This paper describes the design and synthesis of lipophilic isosteres of nucleoside triphosphates as potential inhibitors of HIV reverse transcriptase. The isosteric replacement of the triphosphate group is a modification of the citrate group.