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Efficient synthesis of sphingosine-1-phosphonate and homo-sphingosine-1-phosphonate

✍ Scribed by Andrej Tarnowski; Thomas Bär; Richard R Schmidt

Publisher
Elsevier Science
Year
1997
Tongue
English
Weight
190 KB
Volume
7
Category
Article
ISSN
0960-894X

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✦ Synopsis

Sphingosine can be selectively transformed into 2-N,3-O-protected 1-O-mesyl derivative 8. Transformation into the bromide, Michaelis-Arbusov reaction with trimethyl phosphite, and then removal of all protective groups with LiOH afforded sphingosine-l-phosphonate (4) in high overall yield. Chain extension of 8 with KCN and ensuing reduction led to homosphingosine derivative 10 and also to homo-l-deoxysphingosine (5). 1-O-Mesylation of 10 led via the same sequence of reactions finally to homo-sphingosine-1-phosphonate (6).

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## Abstract Readily available D‐__erythro__‐azidosphingosine is transformed into 3‐__O__‐silyl‐protected derivative 6. Reduction of the azido group afforded 3‐__O__‐silyl‐protected sphingosine 7 which was either converted into __N__‐Fmoc‐protected derivative 8 or via N‐acylation into ceramide deriv