52900-18-2Relevant articles and documents
Synthesis of two Unique Compounds, a Ceramide and a Cerebroside, Occurring in Human Stratum Corneum
Mueller, Silvia,Schmidt, Richard R.
, p. 779 - 784 (2007/10/03)
The cerebroside 1a and the ceramide 1b, both playing important roles in epidermal barrier function, were synthesized by N-acylation of 1-O-glucosylated C18-sphingosine 2 and C18-sphingosine 8, respectively, with O-acyl fatty acid 3. The required compound 3 was obtained from ω-hydroxy fatty acid 6 and linoleic acid 7 by esterification. The ω-hydroxy C30-fatty acid 6 was prepared as follows: Copper-catalyzed coupling of ω-hydroxy alkyl halide 11 with the Grignard reagent derived from bromo compound 13 afforded after oxidation C17-aldehyde 15. Wittig reaction with phosphonium salt 10, derived from ω-bromo-tridecanoic acid 9, and subsequent hydrogenation and O-deprotection furnished 6 in high yield.
