(R)-3-METHYLHEPTANOIC ACID Usage And Synthesis

Description

(R)-3-methylheptanoic acid and (S)-3-methylheptanoic acid are a pair of chiral compounds. Their synthesis is based on the chiral methyl derivatives 3 and 4 of (R)-4-methyl-δ-pentalactone as starting materials. (R)-3-methylheptanoic acid is a component of the abdominal sex-attracting secretion of male Kheper ni groaeneus dung beetle.[1]

Definition

ChEBI: 3R-Methylheptanoic acid is a medium-chain fatty acid.

Synthesis

The synthesis of the (R)-3-METHYLHEPTANOIC ACID 2 from ester 4. Starting from the right side, reduc tion with LiAlH4 followed by Swern oxidation, allowed to convert ester 4 into aldehyde 10, which underwent Wittig olefination smoothly to provide alkene 11 in high yield. Hydrogenation of the double bond and removal of the MOM ether in 11 gave alcohol 12 whose newly ex posed hydroxyl was employed to expand one carbon. From 12, a three-step sequence involving sulfonylation (TsCl in pyridine), cyano substitution (NaCN in DMSO) and hydrolysis of nitrile (reflux in sulfuric acid/water) gave the desired (R)-methylheptanoic acid 2 over three steps in 83% yield. The enantiomer excess of 2 was measured by its derivative 15 to be 95.6%.[1]

References

[1] Shunji Zhang, Weisheng T., Yong Shi. (2015). Syntheses of (R)- and (S)-3-Methylheptanoic Acids. Chinese Journal of Chemistry, 33 6, 674–678. https://doi.org/10.1002/cjoc.201400861

(R)-3-METHYLHEPTANOIC ACID(57403-74-4)Related Product Information

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