199341-35-0

Upstream product

• 77862-72-7 (5-oxo-[1,3]dioxolane-4,4-diyl)-bis-acetic acid dimethyl ester 
• 199341-36-1 C₈H₁₀O₇*C₈H₁₁N 
• 77-92-9 citric acid 
• 4767-12-8 4,4-(5-oxo-1,3-dioxolane)diacetic acid anhydride 
• 144-16-1 5-oxo-1,3-dioxolan-4-ylidenedi(acetic acid) 
• 184834-31-9 [-(2-methoxy-2-oxoethyl)-5-oxo-1,3-dioxolan-4-yl]acetic acid 

Downstream Products

• 173934-26-4 (R)-(-)-homocitric acid lactone 

Relevant academic research and scientific papers

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.

Regio- and enantioselectivity of the enzyme-catalyzed hydrolysis of citric acid derivatives

The hydrolysis of triethyl citrate in the presence of three serine proteases (chymotrypsin, subtilisin BPN', subtilisin carlsberg) is highly regioselective and gives the symmetric diester. Several lipases and proteases have the complementary regioselectivity and give the chiral diester. Pig liver esterase, Aspergillus niger lipase and Candida antarctica lipase give the chiral (R)-diester with good regio- and enantioselectivity. The stereoselective hydrolysis of the meso citric derivatives 7a,b in the presence of Candida antarctica lipase gives the corresponding (R)-monoester.

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.