Regio- and stereocontrolled synthesis of d-erythro-sphingosine and phytosphingosine from d-glucosamine

✍ Scribed by Teiichi Murakami; Hiroyuki Minamikawa; Masakatsu Hato

• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 355 KB
• Volume: 35
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)75806-0

✦ Synopsis

AbstracL Deryrhro-Sphingosine (1) and phytosphingosine (2) have been efficiently synthesized from D-glucosamine by utilizing its whole carbon skeleton and functional groups. In this synthetic route, regioselective alkylation of the epoxy-tosylate 9 was achieved with a copper(I)-catalyzed Grignard reagent to give the bjey intermediate 10, which was converted to both 1 and 2 via regioselective formation of the iodohydrin 11. D-eryrfrro-Sphingosine [(2S, 3R, 4E)-2-aminooctadec-4-ene-1 ,Zdiol] (1) and phytosphingosine [(2S, 3S, 4R)-2-aminooctadecane-1,3,4-trio11 (2) are major backbone components of glycosphingolipids, which play important roles in biological processes on cell surfaces. 1 Sphingosines have attracted considerable interest as potent inhibitors of protein kinase C, an essential enzyme in cell regulation and signal transduction.2 Various synthetic apprcaches to optically active l3 and 24 have been mported in the past decade in view of their biological importance.