112031-18-2

Usage

Uses

Used in Pharmaceutical Industry:
Tetradecanoic acid, 3-(phenylmethoxy)-, methyl ester, (S)is used as an intermediate for the synthesis of (R,S,S,S)-Orlistat (O686480), which is an isomeric impurity of Orlistat (O686500). Orlistat is a medication used to aid in weight loss and is known for its modulatory activity on endocannabinoid 2-arachidonoylglycerol metabolism. The synthesis of Tetradecanoic acid, 3-(phenylmethoxy)-, methyl ester, (S)- is crucial for the development of pharmaceuticals targeting weight management and metabolic regulation.

Upstream product

• 28715-21-1 (R)-3-hydroxytetradecanoic acid 
• 74794-26-6 (3R)-1-trimethylsilyl-tetradec-1-yn-3-ol 
• 73501-40-3 tetradec-1-yn-3-one 
• 77889-04-4 (R)-(-)-1-tetradecyn-3-ol 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 76835-67-1 (S)-methyl 3-hydroxymyristate 
• 76062-97-0 methyl (R)-3-hydroxytetradecanoate 

Downstream Products

• 138650-28-9 (S)-3-benzyloxytetradecan-1-ol 
• 138650-27-8 (S)-3-benzyloxytetradecanal 

Relevant academic research and scientific papers

Asymmetric synthesis of tetrahydrolipstatin and valilactone

The highly diastereoselective aldol reaction between acyl complexes of the iron chiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)] and β-hydroxy aldehydes (obtained via a Noyori asymmetric hydrogenation), followed by a tandem oxidative decomplexation-cyclisation process gives access to β-substituted and α,β-disubstituted β-lactones in high ee. This methodology has been employed in the asymmetric syntheses of tetrahydrolipstatin and valilactone.

A Convenient Benzylation Procedure for β-Hydroxy Esters

Benzylation of β-hydroxy esters, containing primary and secondary alcohol functions, with benzyl 2,2,2-trichloroacetimidate gives the corresponding benzyl ethers in good yield.In the case of chiral substrates no racemisation is observed.