867010-80-8Relevant academic research and scientific papers
Efficient stereocontrolled synthesis of sphingadienine derivatives
Murakami, Teiichi,Hirono, Reiko,Furusawa, Kiyotaka
, p. 9233 - 9241 (2005)
Sphinga-4,8-dienines, principal long-chain bases of glycolipids in plants and fungi, were efficiently synthesized from l-serine. Hydrozirconation of pentadec-5-en-1-ynes followed by ZnBr2-catalyzed addition to Garner's aldehyde afforded protected sphinga-4,8-dienines stereoselectively. The (2S,3R,4E,8E)-9-methyl-sphingadienine derivative was then coupled with 2(R)-acetoxypalmitic acid derivative prepared via asymmetric dihydroxylation to give a protected ceramide, which was converted into the corresponding glucocerebroside in two steps.
