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A simple and low cost synthesis of d-erythro-sphingosine and d-erythro-azidosphingosine from d-ribo-phytosphingosine: glycosphingolipid precursors

โœ Scribed by Richard J.B.H.N. van den Berg; Cornelis G.N. Korevaar; Gijsbert A. van der Marel; Herman S. Overkleeft; Jacques H. van Boom

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
210 KB
Volume
43
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

D-erythro-Sphingosine (1) and D-erythro -2-azidosphingosine (2) are both prepared from commercially available and cheap D-ribo -phytosphingosine (3) in a yield of 58% and 70%, respectively. A key transformation in the synthesis of D-erythro -sphingosine (1) is the palladium catalyzed regiospecific reduction of the Z-enol triflate 9. A crucial step in the synthesis of azidosphingosine 2 comprises a regio-and stereoselective in situ trans-elimination of the 4-O-triflate of azidophytosphingosine 13.

๐Ÿ“œ SIMILAR VOLUMES

Regio- and stereocontrolled synthesis of
Regio- and stereocontrolled synthesis of d-erythro-sphingosine and phytosphingosine from d-glucosamine
โœ Teiichi Murakami; Hiroyuki Minamikawa; Masakatsu Hato ๐Ÿ“‚ Article ๐Ÿ“… 1994 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 355 KB

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 re