Process for the synthesis of acylated derivatives of fatty acid-

Details Process for the synthesis of acylated derivatives of fatty acid- Process for the synthesis of acylated derivatives of fatty acid-

1994-03-18

1995-06-13

Lilling, Herbert J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C07H 1700

Patent

active

054244153

ABSTRACT:
The invention relates to a process for the synthesis of an acylated derivative of a fatty acid-transporting thiol such as the coenzyme A. According to this process, a silylated or stannylated thiol is prepared by reacting the thiol with a silylation or stannylation reagent in order to at least partly replace the unstable hydrogens of the thiol by SiR.sub.3 or SnR.sub.3 groups with R being an alkyl or aryl group. The silylated or stannylated thiol is then reacted in an anhydrous organic medium with an activated organic acid and a deprotection reagent able to eliminate the silyl or stannyl groups. In this way it is possible to obtain acylated derivatives of the coenzyme A, in which the acyl group can have up to 30 carbon atoms with high yields.

REFERENCES:
Chemical Abstracts, vol. 109, No. 9, 1988, AN-68917d, T. Saitoh, et al., "Activation of Synthesis Hexacosenoic Acid by Sulfhydryl Reagents in Swine Cerebral Microsomes".
Chemical Abstracts, vol. 112, No. 21, 1990, AN-195482v, A. H. Vaz, et al., "Sex Pheromone Biosynth Housefly: Evidence for the Regulation of the Fatty Acyl-CoA Desaturation and Elongation System by 20-Hydroxyecdysone".
Chemical Abstracts, vol. 109, No. 13, 1988, AN-106618s, T. Saitoh, et al., "Inhibitory Effect of Very-Long-Chain Monounsaturated Fatty-Acyl-CoAs on the Elongation of Long-Chain Fatty Acid in Swine Cerebral Microsomes".

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