Synthesis of 2-Carboxy-Substituted Sphingosine Derivatives
Title:
Synthesis of 2-Carboxy-Substituted Sphingosine Derivatives
Author:
Singh, Narrinder P. Giannis, Athanassios Henk, Elfi Kolter, Thomas Sandhoff, Konrad Schmidt, Richard R.
Appeared in:
Journal of carbohydrate chemistry
Paging:
Volume 9 (1990) nr. 5 pages 543-559
Year:
1990
Contents:
From the sphingosine biosynthesis pathway it is deduced that 2-carboxy-substituted sphinganine derivatives should be suitable inhibitors of sphingosine biosynthesis. For their synthesis enantioselective acylation and α-hydroxyalkylation of serine was performed via its optically pure 2-tert-butyl-oxazolidine derivatives 4A, B and ent-4A, known to undergo partial chirality transfer from serine to the 2- position of 4 and then to the 4-position. Thus, after acid hydrolysis compounds R-7Aa, -7Ab, -7Ac, -7Bb, S-7Aa, -7Ab, and 11 are provided highly stereoselectively.